you got me all twisted up
18+ account - minors do not interact
jack abbot x f!reader Rating: E
Summary: Jack was no better than Robby when it came to relationships. He moved through life after his divorce using intimacy as a distraction rather than a connection. And then… he met you.
Warning: (MDNI 18+) acquaintances to lovers, wealth advisor reader (girl boss and very successful), starts off slightly angsty (jacks deployment and leg), mentions of infidelity, emotionally constipated jack, he fucks an original character (not descriptive at all, allusions of smut only), fuckboy/commitment phobe jack? language, competency kink (jack is very turned on by your intelligence), flirting, sexual tension, jacks intense eye contact, alcohol, feelings, mutual pining, reader has a dog, mentions of men threatened by success (your ex sucks), pet names, making out like teenagers (they cute and horny), some lite sexual touching / heavy petting, dirty thots, mentions of sexy time, fluff alert, domesticity, I think that’s it
A/N: There’s totally a joke/interaction in this fic that I saw on this post, and I want to emphasize how funny this is. I did not come up with this. Full credit to @tanley GIF by @pittgifs found HERE.
Thank you for reading!! if you comment/reblog i love you so much <3.
For 5 years, Jack had been a husband. He wore the ring, paid the bills, and was building a life with his wife.
His second deployment occurred a couple of years after he made attending, which felt like a brutal, unnecessary interruption. The deployment was a 15-month stint. He served 10. The last 5 were erased in the flash of an explosion. The concussive roar replaced time with pain. He wasn't granted a graceful homecoming; he was medically discharged, shipped back to the States for good, and now a broken piece of 'machinery'.
He arrived home on a Thursday, the details blurred by painkillers and disorientation. Jack's wife helped him to the couch after crying profusely, her touch careful, and avoiding the bulky dressing on his residual limb. When she finally announced the pregnancy a couple of days later, it had felt like a miracle. He had gotten that last home visit at the 8 month mark of his deployment, when they had been intimate together. The doctor confirmed that she was about 10 weeks along.
That baby became his reason. The thought of holding his child fueled the brutal pain of learning to walk again on a prosthetic. For 5 months, he pushed through the agony of phantom limb pain and the pitying looks he received. All because he just cared about one thing: the image of a tiny hand in his.
The confession didn't come in a fight. It came one evening, over a beautiful dinner she had cooked. He was talking about converting the spare room and about safe paints for a nursery. His voice—full of fragile desperate hope finally broke something in her.
She put her fork down. The click of ceramic on wood was the loudest sound in the world.
"Jack," she said, and her voice was terrifyingly calm. "We need to talk about the baby."
He froze, a piece of chicken halfway to his mouth. "What about the baby?"
She took a breath, her eyes fixed on the tablecloth. "I don't… I don't know if it's yours."
The words hung in the air.
"W-what?" he stuttered.
"There's… there's someone else." The admission was flat, drained of all emotion except a weary finality. "Another teacher at the school. It started… after you deployed. It's… It's serious. I think I'm in love him."
Her reasoning, when she finally offered it, was delivered with a chilling simplicity. He worked too much, she explained. He was never there. He worked all the time. All the long hours at the hospital—it felt like his job always came first. Then the deployment was the nail in the coffin. She felt alone, and the other man was just… there. Present. It wasn't a grand passion, she insisted; it was an easy, gradual slide into something that felt like being seen again.
The final unraveling was a cold, clinical procedure. The test results, a single sheet of paper, held the definitive verdict: 0.0% probability of paternity. She filed the divorce papers alongside the test results. There was no discussion of custody, no debate over visitation. He lost his wife to a man he had never fucking met, and he lost a baby that had never been his to lose. All that remained was the hollow, grinding pain in a leg that wasn't there, and the silence in his sad apartment with no spare room to convert.
He was furious for years. It was easier that way. He was the wronged party, after all.
But therapy, and the grim finality of his divorce, had sanded the anger down to a cold, hard truth. She hadn’t been completely lying. The job had come first. Jack had thought that providing was love. He had been a good doctor, a good soldier, but an absent husband. Maybe he just wasn't built for marriage. Maybe his capacity for that kind of priority was broken.
Since his divorce, he was in a self-imposed exile from commitment. He dated, if you could call it that. He had casual relationships. He slept around. The first time after the divorce was nerve-wracking. It had been 2 years of "celibacy" before he met a beautiful graphic designer at a bar. In her dimly lit bedroom, the process of removing his prosthetic felt like some grotesque unveiling. His hands fumbled, his mind racing with imagined disgust. But she had just watched, her expression calm, then reached out and placed her hand over his, stilling the frantic movement. "It's okay," she said, simple as that. He truly appreciated it.
Experiences varied after that. Some women asked thoughtful, clinical questions about the amputation and the mechanics of the prosthetic. Others asked nothing at all, treating it as just another piece of clothing to be discarded. A few were awkward, their eyes flicking to it then away, their touch becoming hesitant. He learned to read the signs quickly. He preferred the ones who asked nothing; it allowed for a cleaner, more transactional intimacy. He became proficient in the art of the uncomplicated exit. A shared meal, a drink, a night in his bed or theirs, and then the gentle, firm disengagement. He was always kind, very generous, but emotionally impenetrable.
He was just as bad as Robby, but he never shit where he ate because the hospital was sacred ground, his last remaining temple of purpose and order. However, the core compulsion was the same as his buddy's: Use intimacy as a distraction, not a connection. A way to feel something without the risk of feeling everything. The relationships, such as they were, never went anywhere. He couldn't bring himself to commit. Not to a shared calendar, not to meeting friends, certainly not to the terrifying vulnerability of a future. He had done it once, with the full force of his being, and it had failed catastrophically. The memory of that failure was a more effective barrier than any physical limitation. He built a life that was professionally fulfilling with incredible friendships. Jack was, as he told himself, content. He had his work, his routines, and his pleasant physical connections here and there. It was enough. It had to be.
And then… he met you.
The hotel room smelled of stale air conditioning, cheap floral room spray, and sex. The muted glow of a floor lamp cast long shadows across the rumpled king-size bed. Jack stood by the window, his back to the fucked out form of Layla, a flight attendant based in Dallas that he had met casually a few months ago. They sometimes fucked whenever she was in town. She had taken a long layover to see her sister, who lived in Pittsburgh. They were going to go to dinner tonight. So, Layla suggested that she and Jack quickly grab drinks at her hotel bar midday. Her flight was at 7 AM tomorrow.
Jack was already pulling on his scrubs since he had 20 minutes to get to the hospital for the night shift.
On the bed, Layla stirred, the sheets rustling. She propped herself up on her elbow. He sat on the edge of the mattress, not necessarily to retreat, but to be closer as he pulled on his shoes.
"The walk of shame, but in scrubs. It's hot," she teased, watching him dress with a soft, sleepy smile on her face.
"Shame's not in my vocabulary," he quipped. Jack finished tying his shoes and didn't immediately stand. Instead, he leaned back on one arm, turning his body to face her fully on the bed.
She pouted playfully, tracing a finger along the seam of his scrubs. "Too bad you have to leave. I'm suddenly feeling a little... off. My heart's racing. Temperature's definitely elevated." She guided his hand, placing it over her bare chest just above the sheet. "Feel that? Irregular rhythm. Might need a doctor."
A slow, wolfish grin spread across his face. He reached out and gently hooked a finger under the edge of the sheet, tugging it just a fraction lower.
"Diagnosis: acute intoxication. Cause: exceptional company. Prescription..." He leaned in, capturing her lips in a kiss full of the heat they had just shared before pulling back just enough to speak against her mouth."...a strict regimen of remembering every detail of the last hour until the next dose can be administered."
"Mmm, a delayed-release treatment. Cruel." She nipped at his jaw. "What if the symptoms get worse… maybe I need to schedule a return trip?"
"You have my number," His tone was light, almost dismissive as he checked his watch. "My real patients are waiting. Try to get some good sleep tonight before your flight, Layla."
He didn't wait for a reply. He gave her one last charming… but ultimately empty smile. Jack grabbed his wallet and keys from the dresser, then quietly opened the hotel room door and stepped into the hallway, closing it softly behind him without looking back. The drive to the hospital was a quiet transition. The ghost of Layla's perfume on his scrubs faded with the cold air from the AC vent. By the time he parked in the staff garage and walked through the automatic doors of the ER, he was ready to get to work.
The day shift team was bleary-eyed, finishing notes and handing off patients, while the night shift (Jack's nightcrawlers) was slowly filtering in. Jack stood near the main nurses' station as Robby slapped a printout onto the counter between them.
"You get to stroll in just in time for mandatory fun. 'Financial Strategies for New Attendings.' Conference Room B. Starts in five. Admin wants you as the night shift lead present for 'continuity' or some other HR bullshit buzzword."
Jack took a slow sip of his coffee, his expression one of amused tolerance.
"Continuity of boredom, maybe. But I'll suffer through. Ellis formally accepted her attending position last night." A genuine, proud grin broke through his usual cool facade. It was rare for residents to stay in the same hospital. Residents usually finished training and then took attending jobs elsewhere.
"Yeah, it's official. King, too." Robby said while shuffling his own paperwork. "She went to the AM session."
"Best part of this damn job is watching the good ones climb."
"Alright, Captain Midnight." Robby clapped Jack on the shoulder, a gesture of weary camaraderie. "The ship is yours. And for God's sake, get some real coffee."
Jack turned, his gaze sweeping over Shen, who was walking in—and of course sipping on his Dunkin coffee.
"Shen. Can you handle handoff with Robby? I have to be somewhere shortly."
"Sure thing," the junior attending replied.
Shen and Robby's conversation was suddenly a rapid-fire exchange of patient statuses and pending labs. Jack stood nearby, and he caught Ellis’s eye as she entered the bay.
"Alright, people." Jack's voice cut through. "Brief intermission from the usual programming." He waited a beat for the nearby chatter to die down. "For those who haven't heard the good news—Dr. Ellis is one of our new trauma attendings!" He started the applause himself, with a few sharp, loud claps. Some of the day shift who were still here, along with the trauma night shift team (other attendings, nurses, residents, techs), joined in immediately.
Ellis offered a humble wave, but the excitement in her eyes was undeniable.
"C'mon, Ellis," Jack started, "Your first official duty is absorbing an hour of financial literacy. Consider it your 'welcome to a real salary' tax."
Ellis groaned.
"Look, it's not all bad. It's the 'how not to blow your first attending paycheck on stupid shit' talk. Boring, but useful." He began guiding her toward the doors, then paused, looking back at Dr. Shen. He was already immersed in the patient handoff with Robby.
"Also, Shen? Make sure to do the chant. It's important for the team."
Shen didn't look up from his tablet, giving a dismissive wave. "Yes, yes, I'll do the chant."
As Jack and Ellis moved out of immediate earshot, Shen leaned closer to the team, his voice dropping to a conspiratorial whisper. "Please say we did the chant," he rolled his eyes. "The old man will be so upset with me if we skip it. Night crawlers, whoo!"
Robby snorted a laugh, shaking his head as he handed over another chart. Meanwhile, Jack led Ellis into the quieter hallway, the distant, half-hearted echo of a team chant (or perhaps the promise of one) fading behind them
"Congratulations are still in order, Ellis. Seriously. You earned every bit of it."
"Thank you, Dr. Abbot. It still doesn't feel entirely real."
He chuckled, pushing open the door to Conference Room B. The room was set up classroom-style, with a presenter at the front facing away and clearly setting up. There was a scattering of other newly minted attendings from various departments at the hospital. He was about to slump into his own seat when the presenter at the front of the room turned from the projector screen to face the audience. Jack stopped mid-motion, his hand still on the chair back.
He registered a woman's face. And… it wasn't just attractive; it was fucking disarming.
Gloria's voice cut in from the side, and she introduced you by name. She explained that you were a wealth manager at one of those fancy schmancy firms, "…our presenter,"
Then, as Gloria spoke, Jack's gaze inadvertently dipped. You were leaning slightly against the podium. He caught the elegant line of a knee-length charcoal skirt and the subtle shift of fabric. He looked away immediately, a reflexive, almost guilty flick of his eyes back to your face. He didn't mean to notice. He really didn't want to be that guy.
"…Brown undergrad…" Gloria continued.
You smiled then, a brilliant, genuine flash of white teeth as you acknowledged Gloria's introduction. The smile transformed your face from severe beauty into something warm, approachable, and utterly captivating. It reached your eyes, crinkling the corners slightly.
Gloria kept rattling off your credentials and the firms you had worked at,"…Harvard Business School, and more than a decade on Wall Street before pivoting…"
Jack slowly sank the plastic chair, which creaked under his weight. He wasn't a stranger to beautiful women, but there was a specific potent alchemy taking place here… It was the razor-sharp focus in your eyes meeting the unexpected warmth of your smile. It was wrapped in a package of undeniable sophisticated allure. You were intoxicating.
"...to wealth management. We're truly lucky to have her."
People started clapping, and you gave a gracious nod, your hands resting lightly on the podium. You waited for Gloria to sit down before your gaze swept over the attendees—lingering for a half-second on Jack's frankly stunned face before moving on.
What the fuck were you doing in PTMC's sad little basement conference room?
He leaned back, folding his arms across his chest, his attention now fully locked on the front of the room.
Ellis smirked.
The polite applause died down. You let the silence hang for a moment before you spoke.
"Before, I get started. Everyone in this room... without a single shred of exaggeration... is a superhero." You let the word hang there, your voice thick with sincerity. You shook your head slightly, as if marveling at the fact. "You are walking into rooms every single day where people are at their most terrified and their most vulnerable. You hold hands and deliver unbearable news with more grace than should be humanly possible." Your own hands came together in front of you with your fingers loosely interlaced. Congratulations. Not just on becoming attendings—which is a massive, huge accomplishment. But… for choosing this path every single day. And most importantly... thank you. Thank you so much for saving lives. Every. Damn. Day."
Jack's usual cynical expression was wiped clean. He looked at the new attendings around him who were clapping and high fiving. Tired faces lit up with smiles. Some were surprised, and a few even blinked back sudden moisture in their eyes.He had sat through a dozen of these mandatory workshops over the years. Every other speaker had just always clicked to the first slide, diving straight into compound interest and loan amortization. It was always transactional. Cold. No one had ever started by calling them superheroes. No one had ever thanked them.
"Alright, let's be honest for a second." A small, knowing smile played on your lips. "I know what you're all thinking. What the fuck am I doing here?"
A ripple of low, relieved laughter spread through the room. Jack, who had been staring at you, let out a short, surprised chuckle at your language.
"And I don’t blame you," you smiled, feeding off of it. "But here's the thing—you all are about to experience the most bizarre financial whiplash of your lives. For years, you make what, resident pay? Which is basically no money. You survive on caffeine, cafeteria mystery meat, and the grim satisfaction of keeping people alive." You paused, letting the nods of agreement continue. "And then, almost overnight, you become attendings. And suddenly, you're making… a shit-ton of money. It's fantastic… but it's also terrifying. Let me use my cousin as an example—he's a cardiothoracic surgeon, and he's definitely my aunt's favorite child."
The room laughed again.
"So, my cousin finished his fellowship a few years ago. He got the fancy title, and the massive paycheck landed. First thing he did? He bought a beautiful house. A $1.5 million dollar house. Because he deserved it, right? He earned it. Then, surprise, his wife got pregnant—baby on the way. Amazing. But now, between the monster mortgage, the prenatal everything, the life insurance he suddenly needed, and the new Volvo he just had to have… the pile of 'deserved' expenses started looking a lot like a mountain of debt. The money that felt infinite suddenly had very real, very large holes in it."
Your gaze swept the room, landing briefly on a few nodding faces before settling, almost casually, on Jack. He was leaning forward, elbows on his knees, completely still. His eyes were locked on yours.
"He's a brilliant surgeon. He can crack a chest and rebuild a heart. But he had zero framework for what to do with the money that skill generated. That's the disconnect. That's the whiplash. And nobody talks about it, because talking about money feels… vulgar. Especially when you've just started making it."
The room was quiet, absorbing the story. A new attending in Ortho near the middle, her hair in a messy bun and a coffee stain on her scrubs, raised her hand tentatively.
"Sorry, but... is your cousin okay? Like, financially? Did he have to sell the kid?"
You laughed. It was a genuine hearty sound that Jack wanted to hear more of.
"See? This is why I like doctors. Morbidly practical. No, the toddler was not liquidated as an asset, though I did float the idea when they started looking at daycare pricing." More laughter occurred. You were funny. He liked that. "But seriously, yes, he's fine. We mapped out his plan together when he realized he was in over his head."
A new attending in Peds with folded arms spoke up, his tone curious rather than anxious.
"Okay, but practically speaking, how? How did he actually get out of the hole?"
"The 'how' doesn't really matter," you smiled, tapping the podium lightly with your fingertips. "The point is: don't do what he did. Don't let the first big paycheck trick you into believing you're immune to reality. However, you should absolutely enjoy your life. You've earned a nice dinner. Buy the good whiskey. Get your own fucking place. No more roommates, and no more tiptoeing around or scheduling conflicts when you want to..." your expression turned sly "well, let's just say when you want your bed to be used for more than just sleeping," you delivered with a wink.
The line hit like a lightning bolt. The room didn't just laugh; it erupted. A wave of hoots, hollers, and howls of laughter crashed over you. Someone in the back let out a long, loud wolf-whistle. Jack's eyes were wide, his mouth slightly agape in genuine shocked delight. He looked from you to the roaring crowd and back, shaking his head, but the grin breaking across his face was one of pure, unadulterated approval. Gloria, however, had reached a new level of discomfort. But in the end, she gave a single slow nod as if acknowledging the practical (if indelicate) point about privacy. You grinned, letting the cheer wash over you.
You held up a hand, eventually quieting everyone down.
"Here is your first, your only, and non-negotiable financial directive: Obliterate your medical school loans as fast as you can. Be ruthless." You clicked the remote. A stark, simple statistic filled the screen behind you.
MEDIAN MEDICAL SCHOOL DEBT: $200,000+
AVERAGE INTEREST OVER LIFE OF LOAN: ~$150,000
The numbers sat there, heavy and silent.
"That's not just debt," you continued. "That's a second mortgage on your future, with a variable rate on your soul. Every dollar you pay off early isn't just a dollar. It's a dollar plus the 6, 7, 8 percent interest." You clicked to a new slide. This one had two simple, contrasting images. On the left: a sleek, new car. On the right: a bold, red "$35,000" with a line through it, next to a calculation showing how many months of loan payments that sum could erase.
"So, before any major purchase—" you paced a few steps to the side, “—you should ask yourself: Is this a payment I could have thrown at this debt instead?" As you finished the sentence, you reached for the top button of your tailored blazer, popping it open. You shrugged it off your shoulders (the gesture was really one of shedding formality), revealing a crisp, well-fitted white blouse underneath.
You turned back to the room, rolling your shoulders. "Alright," you said, planting your hands on your hips. "Ask me fucking anything."
Nearly every hand in the room shot up immediately. And there, among a forest of arms…was also Jack's.
The room had emptied, the buzz of conversation fading into the hallway. You were carefully coiling the HDMI cable when Gloria appeared at your elbow.
"Really, truly, thank you again. That landed perfectly. We'll definitely be in touch for next year's cycle."
"My pleasure, Gloria. Really. This group was fantastic."
You shared a quick smile as she headed out, and you zipped up your laptop bag and reached for your blazer. Jack was pretending to check his phone, but his posture was stiff. He looked up, made eye contact, then looked down again. Just as you slung your bag over your shoulder and took a step toward the exit, he moved, cutting a path to intercept you near the door.
"Hey. Uh. Sorry to—just wanted to say, that was... really great." His real foot tapped a silent, rapid rhythm against the floor "Seriously. I've sat through a lot of these. They're usually a special kind of torture. That was... actually useful."
You leaned your shoulder lightly against the doorframe, tilting your head. "A special kind of torture, huh? Was it the boring breakdown of mutual funds versus ETFs, or was it the shitty PowerPoint animations on bond yields?"
Jack's composure seemed to fracture. His mouth opened, then closed, and he shook his head in a sharp frustrated motion.
"No, I just mean—" he started, his voice tighter now, but you didn't let him finish.
You cut him off (not with words) but with a soft, understanding laugh. You held up a hand with your palm out, motioning a gentle 'you're fine' signal.
"I know. I know what you meant. This stuff isn't exactly the sexiest topic."
"Look, I... I really did appreciate the session. Seriously. You could tell the other attendings were actually listening for once, not just scrolling on their phones." He let out a short, awkward chuckle, his hand rising to rake nervously through his slightly unruly curls. He left his hand tangled there for a moment. "Hell, even Gloria looked awake." As he spoke, his other hand, the one not buried in his hair, found the seam of his scrubs pants, his thumb rubbing back and forth over the fabric in a quick, anxious rhythm. He caught himself doing it and abruptly shoved both hands into his pockets. An hour ago, Jack had been balls deep inside a woman. His hands knew exactly what they were doing. Why were they fumbling now, all over the place? He was standing here like a fucking intern who just got paged to a code blue for the first time. Why couldn't he have just said the workshop was good and walked away?
He decided to change topics.
"So, how did you get involved with this?" he asked curiously. "Not exactly the typical volunteer gig."
"My mother was in a car accident last year. A bad one. PMTC took care of her." You paused, the memory clear in your eyes. "The care was... it was everything. The nurse who was on my mom's case mentioned the hospital was looking for volunteers for financial literacy outreach. It seemed like a good way to help the hospital and pay it forward."
"How's your mom doing now?" he inquired with genuine concern. He didn't want to ask specifics just in case it was a triggering question. However, Jack noticed the slight, almost imperceptible widening of your eyes—a flicker of surprise at the question.
"Incredible, thanks for asking."
He nodded slowly, filing away the good piece of news in a place that usually stored harder things.
"Who was the nurse?"
"Dana Evans."
At the mention of the name, a warm smile broke across Jack's face, transforming his previously tense expression.
"Dana's great. I'm glad she was on your case. She practically runs the damn place. He shook his head slightly. "No, she does run it. We just pretend we're in charge."
The sound of your soft giggle at his comment made him feel like he was on top of the world.
"So, if she runs the place... what do you do?"
"I'm Dr. Abbot. Um. Jack." He extended his hand toward you, his movement now steady and sure. "Night shift chief senior attending.
"Nice to meet you," you shook his hand. He fell into step beside you as you both moved out of the room and into the dimly lit hallway of the administrative wing.
"Can I get your number?" He blurted it out, the question cutting through the comfortable silence. The moment the words were airborne, he seemed to recoil from his own abruptness. "I—uh—mean your work number," His steps faltered for a half-second. You turned your head to look at him, and a smirk touched your lips. "I've actually been... thinking about restructuring some things. My portfolio's a little too conservative, maybe." He gave a small shrug, trying to make the lie sound smooth. "Could use a second opinion."
"The minimum account sizes we usually work with are usually $2 million," you stated, your voice devoid of inflection, simply stating a fact. "The clients we typically work with are generally those with a minimum net worth of $15 million or more."
Jesus Christ. The fact that the hospital landed you as a speaker was a miracle.
"Oh." The sound was a soft exhale, all the air leaving his lungs. "Yeah. I... I definitely don't fit that criteria." He swallowed, his gaze dropping to the floor for a moment before meeting yours again. "At least not the ladder."
"Not the latter," you repeated with an intrigued murmur. "Interesting clarification, Dr. Abbot."
"Jack." The correction was immediate. "Please. Just Jack."
Without a word, you shifted your laptop bag on your shoulder, unzipped a compartment, and retrieved a sleek matte black business card holder.
"Like I said—Jack," you emphasized his name. "I really respect PMTC. What they did for your mom... that matters to me. So here's my offer… forget the minimums. That's for my other clients." You gestured dismissively, as if swiping those imposing figures off a whiteboard, and then extracted a single card and held it out to him between two fingers. He took the card, his fingers brushing against yours, and read your title:
Senior Vice President, Group Director | Private Wealth Management
"You can call the number there. My executive assistant handles my calendar." Your tone was even and very to the point. "She can schedule a high-level consult. We can discuss personalized investment strategies that align with your financial goals and long-term priorities. And then, based on that, I can personally recommend you to financial advisors I trust. People who are good, ethical, and who won't treat you like a small fish. People who can actually help you build what you want."
He looked at you then, his gaze holding yours just a moment too long for it to be purely about finances. He didn't need advice. He had a VA financial planner he trusted implicitly. Jack just needed a reason (any fucking reason) to see you again, and this was the one he'd grabbed onto. He didn't see a ring on your finger, and that didn't necessarily mean you were single, but... fuck, he hoped it meant that you were.
"How much would this cost me?" he asked, the question rough. "Quite frankly, I don't think I can afford you."
"It's on the house."
He shook his head, a stubborn, flustered set to his jaw. "I can't accept that. It's... too much. I can't just take your time for free."
"Consider it my investment in some good karma, then," you murmured, shooting him a deliberate flirty wink.
You turned before he could formulate a response, and Jack simply watched you walk away. And yes, his eyes tracked the sway (and fucking) gorgeous, maddening curve of your ass in that skirt. But as the distance grew, the feeling that settled over him was confusing. It wasn't just lust. He wanted to know you. He wanted to understand the mind behind those sharp eyes. He wanted to know what you read, what you hated, what you dreamed about. It was a wanting that felt dangerously like the beginning of something… and it fucking terrified him.
You hated admitting that when your executive assistant, Pam, had put the call sheet on your desk with 'Dr. Jack Abbot - Personal Finance Consult' scribbled in the margin, your pulse had done a stupid, traitorous little jump. You had clocked him during the workshop because while the other attending checked their pagers or doodled on handouts, his eyes (those fucking intense hazel orbs) had been fixed on you. Not on your PowerPoint slides, not on the bullet points about 401(k) rollovers, but on you. He was listening with a focus so absolute that it had felt like a physical weight in the room. It had thrown you off your rhythm a couple of times. And when he talked to you… that brief, 5-minute exchange at the end of the session had left you feeling flustered and giddy in a way you hadn't experienced since… god, since forever.
You probably stared at his name on your call sheet for a full thirty seconds before you might have manipulated your schedule. So, calmly, you told Pam to slot him in for the following Thursday at 2 PM, knowing full well that the Thompson meeting was supposed to be there. But old man Thompson had cancelled at the last minute to play golf, and you saw an opening. You could have (should have) filled it with the Henderson portfolio deep-dive. That was the responsible, professional move. Instead, you told Pam to push Henderson back a week with a flimsy excuse about needing more data. A frivolous and utterly uncharacteristic decision.
And now, sitting across from Jack in your office, you were feeling an unprofessional schoolgirl rush of heat and light-headedness. It wasn't just his handsome face. It was the way he was looking at you again. His eye contact wasn't polite; it was intense. When you explained defensive portfolio strategies, his gaze didn't flick to the charts on your monitor. It stayed locked on your eyes, as if he were trying to decode a secret language written in your pupils. When you asked about his risk tolerance, he held that gaze, his answer measured, but his eyes... his eyes were speaking volumes you couldn't quite translate. It was unnerving.
You finished the session on autopilot, sliding the printed portfolio summary across the desk to him. "These are my initial recommendations, Jack. Based on our discussion, a balanced, moderate-growth approach seems appropriate."
He finally glanced down at the summary, his long fingers tracing the edge of the document without picking it up.
"You're in a remarkably strong position," you continued. "You're only in your 40s, with no debilitating debt, solid dual income streams from your profession and the rental property you purchased a few years ago. Your apartment is paid off. Frankly, you have the capacity and the time horizon to be more aggressive. Some of the capital you're currently parking in ultra-conservative savings vehicles could be working much harder for you."
When you finished, he was quiet for a long moment. Which made sense. Financial disclosure was intimate in ways people rarely acknowledged. It wasn't like revealing a secret; it was more like handing someone the keys to your choices, your fears, your discipline, or lack thereof. It represented decisions made, priorities chosen, and risks taken or avoided.
Since he wasn't a formal client with a contract, you had asked him to provide rough numbers and estimates (a ballpark) for your initial assessment since you wanted to respect his privacy.
Your assessment: Jack Abbot was doing just fine. More than fucking fine didn't begin to cover it.
"You're very persuasive…And your assessment is... uncomfortably accurate," he grunted out.
You slid a paper across the desk, placing it deliberately on top of the printed summary. "These are three advisors I respect. They're more... entrepreneurial in their approach. They would likely recommend shifting a significant portion of your low-yield holdings into sectors with higher volatility but substantially higher long-term growth potential."
He ran a hand through his silvering hair—a gesture you were noticing he did a lot. "Can I be honest with you?"
"Sure."
"I have a financial advisor," he admitted.
Your eyebrow arched instinctively, a silent question hanging in the space between you.
"Apparently, a not so great one. Or at least, a deeply complacent one." He let out a short, frustrated sigh. What you just did in 30 minutes… you're obviously very, very good at what you do."
You appreciated his compliment. "Well, that's what second opinions are for. Even the most established plans can benefit from a fresh perspective."
"No… I probably need to let him go and find someone new." Jack's gaze dropped from yours for a split second before coming back. "But, that's not it. I—uh only asked for your business card because—I really wanted to see you again." Then you saw it—a faint, warm flush creeping up the column of his neck, staining the skin above his crisp collar.
You leaned back in your chair.
"What a bold assumption. How do you know I'm single?" you asked, your voice a mix of amusement and direct challenge.
He didn't flinch. The blush on his neck seemed to stabilize, replaced by a look of quiet confidence. "The company website. The 'Our Team' section." He paused, letting the admission settle. "It ended with saying that you love caramel frappuccinos—which respectfully isn't real coffee. It's sugar," you smiled at his dry assessment, "—pickleball, and your 7-year-old Australian shepherd." His smile grew. "There was no mention of a partner. I checked. Thoroughly."
You felt a faint warm heat rise to your cheeks, and before you could stop it, your teeth caught your bottom lip. Your professional facade was crumbling, and for the first time in a long time, you didn't rush to rebuild it. Finally, you released your lip, a faint, tingling sensation remaining where your teeth had pressed.
"That's a rather aggressive form of due diligence, Jack," you teased, feeling an eager warmth in your chest.
"I-I was hoping that—um—I could, uh, take you out sometime? If that's something you would even consider," he asked in a husky voice that felt too intimate for inside your office.
"Yes. I would like that." Your voice was clear and firm, leaving no room for misinterpretation.
"Good. That's... really good."
You were on FaceTime with your best friend, Mya, phone propped up against a stack of books on your dresser while you rifled through your closet. The screen showed her lounging on her couch with a glass of wine, already mid-rant about your outfit choices.
"Girl, if you're trying to get fucked on the second date, you need to step up your game," she said, pointing dramatically at the camera. "That black dress makes you look like you're going to work. Try the red one."
You sighed, holding up a red dress against your chest. "This one?"
"Closer, but still corporate. Where's that lace top I gave you? The black camisole with the thin straps?"
You pulled it from the back and held it up. "Really? You realize it's two sizes too big for my chest, right?
She laughed. "Okay fair. Skip that."
"Must be nice having perfect tits," you teased, slipping on another (shorter and skimpier) dress you thought of and turning for her approval. "How's this?"
"Yes!" she snapped. "Now we're fucking talking. Dr. Night Shift is going to forget how to speak when he sees you in that."
You posed, one hand on your hip. "You're acting like this is a sure thing."
"Honey, your ass in that dress is to die for."
"I guess," you muttered.
The memory of last week flashed through your mind. Jack had kissed you in his car after your first date, like he wanted to devour you with his hands gripping your waist and his tongue sliding hot against yours. The second you invited him inside your place—he froze up. He pulled back just enough to mumble something about covering a shift for his friend and colleague Robby in the morning. Jack looked equal parts frustrated and almost…relieved? After he walked you to the door (such a gentleman), you went home alone, turned on, and were slightly confused.
The good news was that he was an immaculate kisser. The bad news was that you didn't know if he knew how to use his equipment. You were old enough not to need a 3 date minimum. Dating was hard enough without wasting time. Sometimes, you just wanted a good fuck, whether it led anywhere or not. Sadly, your past experiences with men had been mostly disappointing (emotionally, at least), so you preferred knowing early if the sex was bad rather than dragging things out with polite waiting. No more pretending to be coy when you knew what you needed.
"Uh…hello?" Mya said, waving on screen. "You spaced out."
"Just remembering how he kissed me and then totally fucking bailed."
"Classic mixed signals. Tonight you cut through that shit. Wear that dress, and if he hesitates again… tell him your pussy has a schedule too."
You snorted.
"Did you buy your tickets yet?" she asked, already knowing the answer.
"Yes."
"It's just not the same city without you. I miss you."
"I wouldn't miss your opening for anything," you said, and meant it. The grand opening of her gallery was coming up, and you had already marked the date in red on your calendar. You'd been counting down since the day she officially signed the papers on the space. Mya had worked toward this moment for years. Gallery assistant, then manager, then curator. And now, finally, she was a gallerist with her own gallery.
You missed her a lot. She was always begging you to move back to Manhattan. She was relentless about it
"Come home," she would say.
The thing was, you had spent nearly your entire adult life chasing that 80-100 hour grind in investment banking. Mya had never experienced the 5 AM wake-ups for 6:30 client calls, or the weeks without sunlight, or that particular kind of exhaustion that made you forget to call your family back for almost two weeks straight. In an immigrant family, that was unforgivable—they genuinely had been worried you had been kidnapped, and your overprotective father flew in to check on you.
You'd made the pivot 3 years ago into wealth management, and you now had a way more predictable schedule. Suddenly, staying in an expensive city didn't make sense anymore. Moving back to Pittsburgh meant giving up a lot (your incredible Chelsea apartment and even more incredible friends): the skyline, the neighborhood bars where everyone knew your name, the rooftop where you had watched a thousand sunsets, and fuck, the feeling of being in the center of everything. But it meant gaining something too: your family. Sunday dinners. Your mama knowing you were eating real food. Your old friends who still lived here, who got what it meant to be from here, and to be a yinzer in your bones.
Being home had given you back something you didn't realize you had lost over the years: yourself
"I miss you too," you said, watching her nod on the small screen.
"Wait, wait, wait—" she leaned closer to her screen. "Lose the bra."
You reached up and slipped the straps off your shoulders. The bra came free from under your dress in one smooth motion, and you set it aside. Your hands slid inside the neckline, cupping your bare breasts directly. You lifted and squeezed them, adjusting the soft flesh to sit just right in the dress. Once you were satisfied, you winked at her.
She let out a low whistle, then shook her head with a wicked grin. "Go get laid, honey."
Jack walked you to your door, his hand resting at the small of your back. The kiss started soft but quickly deepened, his tongue sliding against yours as he pressed you against the doorframe. His hands found your ass, squeezing firmly while his mouth moved to your neck.
You fumbled with your keys, breaking the kiss just enough to speak. "We can take this inside."
Jack hesitated. "I should probably get home."
You pulled back slightly, studying his face. Your brows drew together as you searched his expression, trying to read what was going on behind those eyes. The way he kissed you made your stomach flip, but the sudden pause left you uncertain. You bit your lower lip, the same nervous habit you'd had in your office when he first admitted he wanted to see you again. Your fingers stayed loosely hooked in his belt loops, not quite letting go.
"What's going on?" you asked, your head tilting as you searched his striking face for an answer.
"What do you mean?"
"Look," you cut in, voice sharp with slight frustration, "is there a problem here? You can tell me if you're not into me like that, but your hands on my ass are telling a different story."
Jack's hands stayed on your hips, thumbs rubbing small circles. "I am very into you. I just—"
"You just what?" you pressed.
Jack hesitated, his eyes looking almost green under your front porch light. "I don't want to rush things."
You let out a small laugh, "Rush? Jack, I'm not some teenager. I'm a grown woman. If you want to fuck my brains out. I'm not exactly offended. The feeling is mutual."
He blinked, clearly thrown, cheeks flushing. "You... really just say what you're thinking, don't you?"
"Yeah," you shrugged. "I guess I do."
He just stood there not responding for quite some time, and suddenly the heat of the moment had evaporated, leaving behind a cold, awkward residue. You pulled away, detangling yourself from his loose grip, and turned toward your front door.
"Well," you said, your voice flat and drained of all its earlier fire. "Um. Okay. These things don't always work out. Have a nice night."
Jack stood in the entryway, watching your back as you fumbled with the lock, and felt something crack open in his chest. The sharp edge of your words—these things don't always work out—hit harder than he expected. He was being honest. He wasn't trying to rush things because he just legitimately didn't know how to date anymore. A lot of women he'd been with since his ex-wife had started the same way: a first meeting, then sex within hours—sometimes a date (or fuck again) afterwards. Or a Layla situation. He wasn't proud of the string of one-night stands that had accumulated over the years, but he was always responsible about it. Jack tested regularly and never took unnecessary risks.
In today's day and age (when dating seriously), was he supposed to wait a certain number of dates before trying to get physical? Or months? He once read an article about a woman who wouldn't sleep with men until they hit the 90-day mark. Jack was willing to become best friends with his right-hand to be respectful and wait for you.
"Wait," he said, the word coming out way more desperately than intended. "Sweetheart… please let me explain."
You paused, one hand still on the deadbolt, and turned to look at him over your shoulder. Your expression was carefully neutral, but he could see the disappointment flickering in your face. "I'd rather do this without standing in heels," you said, with a sigh that sounded like pure exhaustion. It made him feel like an asshole. "You can come inside, but this is not an invitation for anything more," you turned the key and pushed the door open, "as you've effectively killed the mood," you muttered under your breath.
He heard you.
Goddammit. He had actually managed to fuck this up before it had even properly started.
Suddenly, a storm of white and tan fur exploded into the entryway. It skidded to a halt, placing itself squarely between you and Jack. It started barking at Jack with the kind of territorial intensity that made him take an instinctive step back. The dog's hackles were up, protective, and Jack realized with a sinking feeling that even your dog knew he messed up.
"Remmy, sit," you commanded, your voice dropping into a hard, authoritative tone.
Remmy immediately dropped his rear end to the floor, his barking ceasing mid-sound, though his eyes (one blue and one brown) remained fixed very suspiciously on Jack's face.
"Good boy," your voice shifted into something soft and soothing. "It's okay, sweetie," you murmured, kneeling to kiss the top of Remmy's head, your fingers scratching behind his ears. "This is Dr. Abbot. He's just gonna be here for a little bit."
Fuck, he had really messed this up. You were calling him Dr. Abbot again.
"He's harmless," you assured Jack, your hand still gentle on Remmy's head. The dog's tail had started a tentative wag, "Just curious about new people."
Jack's knees cracked slightly as he lowered himself to Remmy's level, mirroring your posture. Up close, he could smell the dog—that warm, earthy scent mixed with whatever shampoo you used on him.
"Hey there, buddy," Jack said quietly, his voice stripped of its usual confidence. If the dog hated him, this was truly over. He extended his hand slowly, letting Remmy sniff his fingers before attempting to touch him. When the dog's tail continued its tentative wag, Jack's fingers found the soft fur behind Remmy's other ear—the opposite side from where your hand currently rested.
Okay, this was a cute fucking dog.
The thought hit him unexpectedly as Remmy's tail picked up momentum, the wag becoming less tentative and more genuine. Jack found himself smiling (actually smiling) at the way the dog's whole back end wiggled with the effort of it, like his tail alone couldn't contain whatever enthusiasm he'd decided to extend to a stranger.
The fur behind Remmy's ears was softer than he'd expected. Impossibly soft. Jack's thumb brushed against it again, and the dog leaned slightly into his touch, which shouldn't have felt like a small victory, but it absolutely did.
"I'm going to take him outside to the backyard so he can go nuts," you announced, as you stood back up, giving Remmy one last pat, and guided him past Jack. Remmy followed, but not without giving a final curious glance over his shoulder at Jack.
"Make yourself at home," you pointed down the hall. "The living room is straight ahead. I'll be back."
Jack walked forward and suddenly found himself standing alone in what was unmistakably a gorgeous space.
High ceilings with crown molding, hardwood floors that were softened by a patterned Persian rug in deep reds and indigos that gleamed under the soft glow of table lamps with cream-colored shades. The furniture was a mix of modern and vintage; a rich blue velvet sofa faced an antique fireplace with a white marble surround, and above it hung a piece of abstract piece of art. There were throw pillows in rich jewel tones scattered across the couch, and a soft-looking cashmere blanket was draped over one arm.
But what caught Jack's attention was the wall to his left.
Your vinyl collection was extensive. Floor-to-ceiling shelving, each record spine carefully organized, and even from a distance, Jack could see the quality of the collection. He moved closer without thinking, his eyes running over the names. It was a collection that refused to be confined to a single era or genre, each spine representing a different mood, a different story, and a different world. There were a ton of artists he didn't recognize as well.
Yet the vinyl was only part of it. The shelves continued across the adjacent wall, now lined with books. Finance textbooks dominated one section—dense, technical volumes with titles that made his head spin. Of course, you had a ton of practical money management books. He also noticed that you read a lot of legal thrillers, autobiographies (some of the same from his own bookcase), and had an extensive collection of cookbooks. It painted a picture of someone endlessly curious—someone who could dive deep into fiction one moment and lose themselves in a stranger's life story the next, only to emerge craving something beautiful to cook.
Next to your books was a shelf of framed photographs. Jack found himself drawn to them, and he was in the process of leaning in when one image made him do a double-take.
There you were, several years younger, standing beside former President of the United States Barack Obama at what looked like a gala. In another frame, you were laughing with a renowned philanthropist he recognized from the news, both of you holding champagne flutes. Candid shots of you laughing with friends, a woman he assumed was your sister, you holding Remmy when he was a puppy, and a picture of you with your arms wrapped around an older couple who had the same warm smile.
His eyes snagged onto another frame. Holy fucking shit, was that a picture of you, Roger Federer, and Rafael Nadal? You looked deep in conversation at what looked like a fundraiser—you had told him you were a big tennis fan.
Jack's mind spun back to your first date. You had mentioned your time in New York, your investment banking days, but you were casual about it in a way that now struck him as deliberately downplayed. He didn't know much about finance—his expertise was in medicine, not markets, but he had a feeling that you were the best at what you did. At your office, he had noticed your back-to-back rankings on your wall from Forbes' Top America's Top Women Wealth Advisors List. The sound of footsteps interrupted his thoughts, and he turned just as you came down the hallway, Remmy trotting alongside you.
You had changed.
The dress (that had been driving him slowly insane) was gone. In its place were soft, oversized light green pajamas that looked so comfortable. Your feet were bare. Freshly painted toenails in a deep burgundy. You had washed off most of your makeup, and somehow you looked even more beautiful—more real.
You settled onto the couch just as Jack moved to sit beside you. Before he could, Remmy wedged himself against your side, curling up possessively and taking up more space than his small frame should have. Jack chuckled and crossed to sit in one of the opposite chairs instead, making himself comfortable across from where you sat. The cushions were soft and smelled faintly of lavender.
"So," you said, your voice neutral. "Explain."
"We haven't really talked about previous relationships much," he started, running his hands over his thighs. "I know I told you I was divorced—"
"You did," you confirmed, and there was no judgment in your tone, but there was a firmness that made it clear you were listening closely.
So, he told you the story, which he hadn't really shared with anyone in a very long time. He let the words tumble out… the whole ugly truth of his marriage. "And well, I haven't really been in a serious relationship since," he said after finished talking. Your arms were still crossed, but your expression had shifted completely. The disappointment was gone, replaced by wide-eyed, stunned disbelief. Your lips parted slightly.
"Holy shit," you breathed, the words hushed. "That's… that's like some Maury Povich shit."
He rubbed a hand over my face. "Ugh. Yeah, I guess."
Then, without another word, you stood up. You just turned and walked out of the living room, leaving him sitting there. Great. He had overshared, and now you were gone? He heard a cabinet open and close in what he assumed was the kitchen. Glass clinked softly. His confusion deepened. Were you getting a glass of water? Preparing to politely ask him to leave?
Jack looked down at his hands, the weight of the entire disastrous evening pressing down on him. Then, he heard your footsteps returning. You walked back into the living room, but you weren't empty-handed. In one hand, you held two heavy-bottomed crystal tumblers. In the other, a bottle of Highland Park. You didn't look at him as you set the glasses down on the coffee table with a soft, definitive clink. You popped the cork, the sound loud in the quiet room, and began to pour. A generous two fingers in each glass. You slid one glass across the table toward him, then picked up the other.
"Bottom's up."
You took a slow sip, your gaze never leaving his over the rim of the glass. Then, you lowered your glass, holding it loosely in one hand. "That's a hell of a story. I thought my ex fucking sucked."
"What happened with your ex?"
You let out a short laugh through your nose. "Nothing like that."
He took a hearty gulp of his drink, his throat working as he swallowed, before turning his full attention back to you. His jeans were worn in just the right way, and the simple t-shirt stretched across his shoulders in a manner that was distractingly good. God, this man was fine as hell.
"Why don't you tell me about it?" Jack said, leaning forward just slightly, and resting his forearms on his spread knees. "I think it's only fair."
The memory rose up, sharp and sour. "I was engaged once."
"Engaged?" Jack's eyebrows shot up.
"Yeah. My fiancé," you said the word like it tasted of regret, "We met in business school—he went to work at his father's firm after we graduated because he couldn't land anything. I got a pretty cool gig, and over time..." you shrugged. "I could just feel it. His resentment. The quiet little digs he made at me."
You remembered the way he would change the subject when you talked about a win at work. You started hiding things. Stopped telling him about promotions, about big deals. You made yourself smaller… to make him feel 'better.' Your sister hated him from day one. Called him a dipshit with a trust fund. Your parents... they tolerated him. For your sake. 'We don't get it, but it's your life.' They had once told you.
"When he proposed, it felt so half-assed," you took a slow sip, the burn doing nothing to chase away the old sadness. "We were at some overpriced steakhouse he picked because he thought it was 'classy.' No knee, just him sliding a ring box across the tablecloth and saying "we might as well" like he was closing a business deal." The memory tightened your chest. "Which is the thing that really gets me—I'll never get that moment back, you know? That should have been special. And he made it feel... mediocre. Like I was a consolation prize he settled for." You finally looked up from your glass, meeting Jack's eyes again. The raw understanding of pain you saw there, without a trace of pity, was more potent than the whiskey. "I said yes anyway. Because I was so fucking in love with the idea of who I thought he could be. I wore that ring for 6 months, feeling it get heavier every day, until I finally took it off and left it on his kitchen counter and moved out." You looked away, your gaze drifting to the dark window, seeing not your reflection but the ghost of your own younger, hopeful face.
"Your ex didn't know what the hell he had." Jack shook his head. "A real man doesn't ask his girl to dim her light so he can feel big—he feels proud as hell watching her shine."
"I'm just tired of the contradiction," you admitted, reaching down to run your fingers through Remmy's soft fur. "Men say they want ambitious women. They say they’re drawn to the drive, but I call bullshit. The moment you actually pursue it…" you sank your hands deeper into his coat, and Remmy leaned into you, his weight solid and grounding, "that's when they start looking for reasons, and suddenly you're 'too focused' or 'not the person they fell for,' or some other lame fucking excuse." Remmy's tail wagged slowly, and he nudged his nose under your hand when you paused. "As if ambition were only attractive in theory, and something charming to admire from a distance," you whispered sadly.
Jack scoffed. "A decent guy wouldn't pull that shit—he'd celebrate your success instead of feeling threatened by it."
You furrowed your brows, the creases deepening between your eyebrows as the weight of his words hit you.
"Hearing it said like that makes the whole thing feel even more pathetic."
"It's not pathetic. You loved someone who couldn't handle being loved by someone stronger than his ego allowed. That's on him, not you."
You started laughing then (really laughing) because the absurdity of it suddenly hit you. "Don't try to make me feel better when your wife tried to pass off another man's kid as yours."
Jack's expression cracked, and then he was laughing too. It wasn't a happy sound exactly, but it was real. You both sat there, shaking with it, the kind of laughter that bordered on hysteria. Remmy lifted his head from where he'd been sprawled across your lap, his expression shifting into clear confusion as he watched you both. He stared for a moment like he was trying to decode what was happening, then hopped down from the cushions with a soft thud. He padded over to his little rug in front of the fireplace (his favorite place) and settled onto it with a sigh, as if to say you two are on your own.
"I'm sorry," you said, catching his breath. "I mean—I guess it's good that she didn't go through with it."
He took another drink. "Yeah, well. Our marriage failing wasn't exactly all her fault. I wasn't exactly a present husband."
"That's not a pass for cheating, Jack…" you set your glass down deliberately, "I haven't known you long, but I have a feeling you're being too hard on yourself. I'm so sorry that happened to you."
Thank god, he thought, the tension in his shoulders easing a fraction. You were calling him Jack again.
"She should have talked to you about how she was feeling instead of just... holding it all inside and then blowing up your marriage like that."
He blinked slowly.
"If she felt neglected, she should have said something. Given you a chance to actually hear her, and to and fix it. How could you have worked on a problem that you didn't know existed?" you shrugged. "She made her choice—to cheat instead of to communicate."
You understood the weight of a demanding job. And sure, you were only hearing his side of the story, but he hadn't even bad-mouthed her—not once. Admitted that he took it too far, and let work consume everything. There was something in the way he talked about his marriage, a genuine regret that suggested he would have made adjustments if he had known earlier on.
"Well, you know what they say…'how you get 'em… is how you lose 'em.' Are they still together?"
"No, they're not… pretty sure he cheated on her, actually. At least that's what my mother says." He paused, deadpan. "My mother's a gossip."
You snickered.
"Look, it doesn't matter what happened between them. That's... that's their thing," he scratched his jaw. "The kid's the one who suffered. Families being torn apart is never easy."
Most people would've been ecstatic at their ex's misery. You hadn't met a lot of guys like Jack. And the fact that he gave a damn about the kid? That told you everything you needed to know about who he really was. He was a good man.
You leaned back, studying him with an expression that was both softer and more probing. "Look, thank you for being honest with me. That couldn't have been easy. But, I'm a little confused? Did you tell me this because you haven't... been intimate with someone since your ex-wife?" You had never been with an amputee (which you learned about Jack on the first date), and you wondered if that was adding a layer of additional nerves for him.
Jack stood up and took a couple of steps around the table and lowered himself onto the couch next to you, close enough that his thigh brushed against yours. Remmy lifted his head and let out a soft, warning whine at Jack's approach.
"Come on buddy, I need a moment with the pretty girl," Jack pouted. You stifled a laugh as Remmy's protective instincts flared. He gave a final assessing look. Then, with a quiet huff that seemed almost like a sigh of resignation, he lowered his head back to the floor. You bit your lip to contain your amusement. Jack turned his body fully toward you then, and he laced his fingers through yours before drawing your hands into his lap.
"Look… I don't want to lie to you. I've been with a lot of women since my divorce," he grunted out. "I'm single. And well…" his sentence trailed off. He didn't need to finish.
You appreciated his honesty. There was an unexpected pang of jealousy twisting in your gut, but you weren't blind. He was attractive. A 'silver fox' doctor with a hot bod and a smile that could melt hearts. Women were probably throwing themselves at him. And honestly…with his history, you weren't shocked he was fucking around. It was probably easiest that way.
"We just met. It's totally okay if you just want to have fun," you tried to sound understanding, to give him an out, and to protect yourself.
His expression grew guarded. "Is that what you want?"
After all this time, Jack felt like he had finally met someone he was fucking crazy about. He barely knew you. It didn't make sense… and he had never believed in perfection.
But goddamn it, you were pretty fucking close.
He was terrified that was what you wanted. Just fun. A casual fling. And he believed that he would deserve it if you did. Over the years, he knew—somewhere in the back of his mind, that some of the women who had left his bed had wanted more. He saw it in their faces the morning after, a hope he deliberately extinguished with a polite smile and a firm goodbye. He was always honest with them about his emotional limitations, but honesty didn't erase the disappointment. Maybe this, you offering him the very emptiness he had offered others, was the price he finally had to pay. Maybe the universe was serving him his own medicine.
"I don't know," you said honestly. You let your gaze travel slowly down his body and back up to meet his. "If you had fucked me on the first date, I might have a better answer," you teased.
He smirked at your sarcasm. But…your playful mask slipped, revealing the genuine uncertainty beneath. You let out a slow breath, a vulnerability appearing in your voice. "I was just going to see how this went," you admitted, your gaze dropping to where your joined hands before finding his gorgeous eyes again. "And not really put any pressure on it." You shrugged, a small, self-deprecating gesture. "Whenever I get excited about something... about someone... it tends to just go south."
Jack's expression softened completely, and he reached out, his fingers gently tilting your chin up so you had to look at him.
"Well, I'd really like to take you on a third date," he said. "I haven't had one of those in a really long time," he joked, the lightness in his tone a gentle counterpoint to the heavy conversation. Before you could formulate a reply, he closed the small distance between you. His hand slid from your chin to cradle the back of your neck, and he kissed you. His lips were warm and insistent, moving against yours in a way that instantly turned you into a puddle. You could taste the faint trace of whiskey, feel the scratch of his stubble, and an extremely embarrassing sound escaped your throat as you kissed him back.
He pulled back just far enough to speak, "I really like you," he murmured, the words a soft, raw admission against your lips. "And I know I'm not supposed to say that, but I can't help myself.”
"I really like you too," you replied and kissed him again, your fingers threading through his luscious hair as he groaned into your mouth.
"I do want to fuck your brains out, by the way," Jack said roughly when you finally broke apart, both of you breathing hard. "Just so we're crystal clear."
You grinned against his mouth. "Maybe we can save that for our next date," you said, fingers still tangled in his silvery curls. "But can I entice you into a respectable PG-13 make out session? I wouldn't be against second base."
Jack let out a laugh that vibrated against your lips.
"Fuck, sweetheart, you're gonna kill me," he muttered, then dove back in to kiss you.
The couch felt smaller by the second. Cushions creaked under shifting bodies. Every wet sound of your mouths moving together filled the space—soft gasps, low groans, the occasional curse slipping out when teeth grazed too sharp. Your pulse hammered in your ears, drowning out everything else except the way his stubble scraped your chin and the heat pouring off his body. You pushed him down onto his back, climbing over him as his hands slid lower. He grabbed your ass hard through the loose pajama pants, fingers digging in, pulling you tighter against the thick bulge in his jeans. You arched into the touch with a shaky moan that made him curse again.
"Jesus, the sounds you make," he breathed against your jaw, then sucked at the spot just below your ear. You tasted salt when you licked your lips, felt the rapid thud of his heart when you pressed closer. His cock strained against his jeans, thick and obvious, pressing up between your thighs every time he shifted.
Jack's thoughts were a filthy loop he couldn't shut off: how tight you would feel when he finally sank his cock inside you, how wet you would get, how loud you would get when he fucked you properly. He wanted to rip your comfortable pajamas off right there on the couch, spread you open, and bury himself to the hilt. But he didn't. Instead, he kept it to heavy petting and desperate kisses, letting the tension build until both of you were panting and half-laughing at how worked up you'd gotten.
Eventually, the kisses slowed, turning softer, almost sweet. His forehead rested against yours, both of you catching your breath.
"Third date can't come fast enough," Jack said.
Remmy barked in agreement.
Sprinklers clicked on in someone's yard as you and Jack made your way back to your place from the neighborhood park. Remmy trotted ahead on his leash, tail wagging like he owned the sidewalk. The proximity to the park had been one of the main reasons you bought the house.
Jack had taken the leash from you halfway through the walk.
You were still typing a reply to Mya about your flight details for tomorrow to attend her gallery opening this weekend when Remmy stopped to do his business. You reached for the roll of bags in your pocket, but Jack was faster. His fingers closed around the plastic before you could pull it out.
"I got it, baby," he said simply, already crouching down. It still threw you off when Jack did that—you could count on one hand how many times your ex had done it in all the years you had dated. He always reminded you that Remmy was your dog since you'd had him since before you two got together. Remmy had taken to Jack fast, and you could tell the feeling was mutual. By the time you reached your front door, the sun had dipped low enough to paint the sky in your favorite shades of purple and pink. Inside, you filled Remmy's bowl while Jack unclipped the leash and crouched on the living room floor playing with him. You pulled out your phone to text your sister and brother-in-law about what time to pick up Remmy tomorrow with their spare key.
Jack was dropping you off at the airport in the morning. He offered, and you said yes without overthinking it. You and Jack were existing in that strange, undefined space where you were sleeping together, seeing each other pretty regularly, but hadn't quite put a name to it.
After your third date (which occurred almost 2 months ago), you learned that his very fucking large equipment most definitely worked. Desperate kisses had turned frantic when he picked you up in his car, and your hands wandered, tearing at each other's clothes. It wasn't exactly the classiest move fucking him before the date. But, later… when you finally did make it to pickleball, the afternoon felt electric, every moment reminding you of what had happened just before.
It was one of the most memorable dates you'd ever had.
You hadn't seen Jack yesterday—he was currently off for 3 days. The night before, you had hosted a dinner with some girlfriends and cooked cheesy spinach & mushroom tortellini. You wanted him to taste it, and you had set aside a generous portion for him to take home so it wouldn't go to waste while you were in New York. The leftovers from last night were still in the fridge, and you pulled it out along with some garlic bread you'd wrapped in foil. The oven beeped as it preheated, and you were sliding the dish inside when Jack appeared behind you. His mouth found the side of your neck, pressing an open kiss there.
"Smells good," he murmured against your skin.
"Thank you," you leaned back into him, just for a second. "20 more minutes."
"I wasn't talking about the food."
Heat bloomed across your cheeks. You turned around and swatted at him without much force, your hand connecting with his forearm as you twisted out of his embrace. He raised his eyebrows, a panty-dropping smirk playing at the corners of his mouth. You felt your downstairs area flutter at the way Jack's smirk lingered, that cocky tilt to his mouth promising trouble. Before you could protest, his hands gripped your waist, and he hoisted you onto the counter in one smooth motion, settling you between the cutting board and the half-unwrapped garlic bread. Your legs dangled, and he stepped between them, palms braced on either side of your thighs.
"20 minutes is a long time," he said, voice all fuckable and teasing. "Plenty can happen in twenty minutes."
"Is that so?" you managed, trying to sound unaffected despite.
"Mmm," he hummed, eyes dropping to your lips. "I could make you come twice. Maybe three times."
Jack didn't recognize himself anymore. He prided himself on understanding the human body—he was a doctor after all. He could explain away attraction, compartmentalize desire as a series of chemical reactions. Except when he looked at you, he didn't just want your body—though God knew he did, constantly, in a way that bordered on pathological. He wanted to know what you were thinking. He wanted to make you laugh just to hear that specific cadence of your voice. He wanted to fall asleep next to you and wake up to your face.
"Jack!" you squealed, swatting at his chest again.
"I'm being honest about my intentions."
"Behave," you warned, but there was no real bite to it.
He caught your wrist gently, pressing a kiss to your palm. "Where's the fun in that?"
A rational part of his brain (the part that had aced neurobiology) whispered about the oxytocin surge during new relationships and well—sex. It created neural pathways and made you seek out that person again and again. Evolutionary biology, really—mammals bonding to ensure offspring survival. It was supposed to be temporary.
So why did the thought of this feeling ever fading away terrify him in a way that made no clinical sense?
"Okay, so..." you started, looking embarrassed. "I feel lame, but I've never actually... you know. On a kitchen counter."
Jack pulled back slightly, his eyebrows shooting up. "Really?"
You were adorable.
"Yeah." You bit your lip, suddenly very interested in the pattern of his shirt. "Maybe that makes me boring."
"You weren't boring the other day when you—"
"Nope." You pressed a finger to his lips, cheeks burning. "We're not talking about that right now."
"We're not?" he asked innocently. "Because I seem to remember—"
"Okay, you know what?" You pulled your hand back and crossed your arms—though your cheeks were hurting from how wide you were smiling. "You're definitely not getting any until after dinner now."
"Are you really going to reject a triple orgasm guarantee?"
You were fighting the urge to cave. Instead, you lifted your chin, meeting his heated gaze head-on. "I'm still going to get it. Just after my belly is full of food and wine."
"Fine," he relented after a beat, stepping back with a dramatic sigh. "You win this round. But you better be my dessert."
He turned to the cabinet and started setting the table without being asked, while you hopped off the counter. The fridge hummed quietly as he pulled open the door and reached for a bottle of wine. His phone buzzed loudly on the counter just then, screen lighting up with an incoming call.
"Dr. Abbot," he answered when he looked at the caller ID, tucking the phone against his shoulder as he grabbed two glasses from the cabinet. He poured wine into the first glass, then the second, and he slid one across the counter toward you, offering it with a quick wink before turning his attention back to the call.
"I can't, actually," he said, his voice slipping into that clinical and very sexy professional tone. "I'm dropping my girlfriend off at the airport tomorrow morning."
Girlfriend?
You caught fragments of the rest—something about trading for a shift, coverage, logistics. His free hand gestured as he talked, wine glass held loosely in his grip.
Girlfriend.
Girlfriend.
Girlfriend.
You felt a little silly suddenly, for all the times you wondered if maybe he was seeing someone else, if this was just a convenient arrangement for him. You weren't needy or clingy or paranoid. But in your defense, men sucked. So yeah, you wondered. You worried. Especially after you two started fucking. You weren't proud of it, but there were definitely times you rescheduled dates (just cause), or took your time texting him back once you realized your feelings were getting stronger. That whole calculated performance of seeming less interested so he'd be more interested.
"Ask Shen if he can cover it," he continued, "but he's working tonight, so I don't know if he'll want to do a double. He did one a couple days ago."
He took a sip of his wine while waiting for a response, eyes meeting yours briefly over the rim of the glass. Remmy suddenly bounded over to his leg, demanding attention. Without missing a beat in his conversation, Jack crouched down, one hand holding the phone, and scratched along Remmy’s neck. Jack was now launching into details about some trauma case. You could tell he was still half-listening to the phone conversation, his responses coming at appropriate intervals, but his attention was genuinely split now.
"I know, I know," he said, this time unclear if he was speaking to the person on the phone or Remmy. Jack's eyes crinkled at the corners, and his hand trailed down to Remmy's chest where he gave a few firm, affectionate pats.
This man literally picked up your dog's shit on walks. Of course, you were his girlfriend. Maybe men his age didn't need to spell things out. Maybe it was implied in the way he would fuck you, pressing you into his mattress, groaning into your mouth: You're mine (or your pussy is mine)
He finished the call a moment later and turned to look at you, his expression shifting to something more curious. "What?" he asked, straightening up from where he'd been playing with Remmy.
You bit your lip, fighting the smile that wanted to break free. "Nothing," you said, turning back to the oven. But it wasn't nothing. It was everything.
After dinner, you both relaxed for a solid twenty minutes to let dinner settle before moving to the bedroom. He did, in fact, make you finish 3 times that night. You made a mental note to christen the kitchen counter for when you returned from your trip.
Let's just say that your boyfriend needed zero convincing.
I'm genuinely passionate about financial literacy (I taught in this space in grad school) so this story was basically my excuse to indulge myself and geek out. I'm treating this as a companion piece to 'You Look Good on Vacation.' I know some people were eager for a certain follow-up scene, but oops, I ended up writing how they met instead. However, this story does provide crucial context for why Jack would be so anxious about making the reader's vacation truly unforgettable. TBD (I make no promises) on that one.
That said, this absolutely works as a standalone if you prefer to read it that way!











