insider trading — h.c.
summary: after seventeen years, it still seems that Harry doesn’t quite know all that he thinks he does.
warnings: none, really. fluff. longtime besties. allergic to communication trope stretched over decades. some things get lost in translation but it shall all be resolved in the end.
note: if you were to look at my several other attempts at writing on different apps, you’d know that i am VERY bad at doing things in a timely manner but hot damn will i get things done before the deadline, even if it’s at the absolute last minute. that being said, here’s my entry for the @pedroscurls PPCU dialogue writing challenge! my prompt was “Wait a minute… Are you jealous?” not gonna lie — half of this was written while i was on my third dosage of Sudafed, and the other half was completed in a casino parking lot waiting for my sister and her friends to finish their birthday celebrations. and considering this is my first attempt at writing after a 2 year break, please take this with a huge grain of salt and don’t look too closely orrrrr you might find many errors. but with that i also hope you enjoy it and it’s worth your time!
wc: 5k
Just another overly-exuberant Castillo function. Glittering glass chandeliers. Extravagant but tasteful floral arrangements at every table and lining the walls. A five-star catering company bustling in and out between patrons as they refilled trays and adjusted platters. Champagne bottles popping every few minutes and flowing into frost-coated flutes. Music, loud and swinging, as guests mingled on the dancefloor, only some actually giving a show of a dance while others laughed and chatted. Guests seated around the round tables as some business deals were finalized over hors d’oveurs and whiskeys, neat please.
Yes. This was the norm for the Castillos. And despite knowing them for the last seventeen years and being invited to more than your fair share of events, seeing the finished product never failed to take your breath away every time you stepped foot in the rented out ballroom on Harry’s arm.
One of the best decisions you could have made while doing undergrad at Columbia was to sit next to Harry Castillo in your Intro to Communication Studies class as a bright-eyed and bushy-tailed freshman. Of course back then you hadn’t known you’d picked a seat next to the son of a Fortune 500 company. All you had seen was a boy with a kind face who looked just as nervous as you to be beginning a class entirely focused on public speaking.
You gave him a smile. He returned it. You introduced yourself. He introduced himself. The professor spoke. And suddenly you and Harry were partners for the quarter.
It took a few meetings for the awkwardness and clunkiness of your encounters to wear off. Between meet-ups at the PUB and quiet conversations in Room 103 before and after class, you and Harry got to know each other and gradually became comfortable around each other. You naturally melded well, which was a blessing considering you two would be working together quite often over the course of the next three months. But in getting to know him, you found you had a fair few things in common. He liked to read, you were a fiend for poetry. He enjoyed a quiet night in over bustling clubs, you couldn’t recall the last time you went out. He hadn’t been able to control the scowl that pinched his face when someone asked if you both wanted to join them on a hike, and you couldn’t help but laugh and share your equal disdain for the outdoors.
Best decision you had ever made.
After the public shame ritual that was a speech class, you and Harry ended up staying in touch and becoming close friends in that freshman year at Columbia University. It wasn’t until the end of the school year that you learned he was Harry Castillo, son of the co-founders of THE Castillo & Lynch Capital: one of the most successful private equity firms on the East Coast. You would have never guessed that his family was that wealthy—he was one of the most humble and down-to-earth men you’d met. His temperament was a breath of fresh air from the sea of cocky, alpha-male type business dudebros in the rest of your business classes.
You met his younger brother, Peter, and his parents that summer while visiting over a holiday weekend. It was quite easy to see where Harry got his kindness and softness from: his family were the perfect hosts for your long weekend stay, they were perfectly chatty and seemed truly interested in learning more about you, and even extended an invitation to their Board Members Ball the next night. You tried to politely refuse, truly, but they were as stubborn as they were nice. They would not take no for an answer.
That’s how you found yourself in attendance at your very first Castillo function. You had been so awestruck back then that it took a few minutes to recalibrate yourself to be an actual human being rather than a fish gaping for air on land. Harry had awkwardly scratched at the back of his neck at seeing your face, offering a half-assed bashful comment on how his mom didn’t know the word “limit” when it came to decorations. “With New York financiers, there really is no such thing as too big.”
Your wide eyes still glittered as you took the scene in. That night, you and Harry and Peter had mostly clung to the sidelines. The three of you were decidedly not business people. Not quite, anyways. You and Harry were in your undergrad pursuing a business degree while Peter was entering his junior year of high school. You three had absolutely no business mingling with businessmen and women. You three did, however, absolutely take advantage of the loose supervision of the free champagne floating around the ballroom on serving trays. You and Harry ended up having to carry Peter home and hide him from their parents as he nursed a tragic hangover that came from too much bubbly in a sixteen-year-old boy.
From then, you’d always been welcomed at the Castillo home. Through college, summer breaks, and even into your first ventures into the “real” world with no safety net and only your hard work to aid your navigation of the job hunt. It was only after a few months of failed interviews and fruitless job searches that you accepted a temporary position with Castillo & Lynch. Temporary. Only until you could get your feet under you, only for the purpose of building connections and networking so that you could soon get a job yourself. If the Castillos had it their way, you’d have stayed with them and worked all the way up to Junior Associate within a year. But you were determined to make a name for yourself and build your reputation on your own rather than relying on the already well-established Castillo name — no riding coattails for you.
Unless, of course, it was on Harry’s arm walking into a party you had no business attending; more so for his comfort than yours. In that case… all bets were off. You suspected that somewhere along the way it had just become a convincing lie he stuck to in order to guilt you into continuing to join him. While your career was much slower in growth, Harry’s skyrocketed. He wasn’t quite a nepo-baby, but he was pretty damn close. He worked hard, explored side ventures, founded start-ups, made his own deals, and was a hell of a businessman on his own, yes. But the Castillo name surely aided him along the way and he soon shot up to the title of Senior Associate within Castillo & Lynch.
And now, here you were, at your umpteenth Castillo function. Another upscale ballroom, another lavish celebration, another half-assed purpose for the whole thing. But hey, seventeen years of these parties had led you to be numb to the extravagance of it all. Rather than a rare occasion and coveted invitation, this was just another opportunity for free booze and a crowd of CEOs and VPs and associates to rub elbows with.
Harry, your unofficial all-but-in-name date for the party, had already mingled in with that specific crowd. Disappointing, but not surprising. He never was one to sit idle and let opportunities pass him by. Somehow after years of attending parties and conferences and weddings together, it seemed that he was just as oblivious to the attraction you felt towards him as the day it began. Not a crush — that was the term you used in university, and childish. No, this was an attraction formed after almost two decades of friendship and close proximity and inside jokes and life — very adult, thank you very much. Probably a good thing that he didn’t notice, though. All this time later and you still had absolutely no idea as to what you would say if he even questioned you about it.
You nursed your drink of choice while surveying the floor, trying to mark the first target you would visit of the night. Let’s see… TA had been looking into expanding into the Northwest… business partners would be a good start… Trilogy? That might be a good place to start. And at the very least, it wouldn’t hurt to build on networking opportunities. There’s Harry with, God, a stunning socialite practically tripping over herself to hold his arm. Well, at least he’ll be busy for the next twenty minutes. Here we go…
…
Another highball later and you felt your cheeks heating as you smiled with the representative for the Trilogy Private Equity firm. Randy, his name was. Your unofficial pitch to him on behalf of TA Associates had gone over spectacularly and you’d quickly exchanged business cards. But now you were just talking with the man, and it was nice. He was kind and quick and funny and a good listener. And so so smooth with the subtle, small hints of flirting he sprinkled throughout the conversation. It was almost difficult to determine when he was intentionally flirting and when he was just chatting and that’s partly what made it so perfect and relaxing. You felt at ease, your shoulders sliding down and your sips of your drink becoming more for fun rather than nerves. You didn’t feel like you had to analyze and decode every word he said for a potential flirt or a loaded link back to business. It was just… nice.
When your ice cube rattled in the glass emptily, he smiled and offered to go grab a fresh round. You thanked him after giving him your preferred drink and watched as he disappeared into the crowd of suits, your cheeks only slightly aching when you realized you were still smiling.
“How’s it going over here?”
You damn near jumped out of your skin. Harry leaned against a chair behind you as you turned around, the picture of casual nonchalance, as if he hadn’t just scared the shit out of you. You fixed him with a light glare — nothing like the withering stares you reserved for boardrooms and negotiations. “I’ll slap you.” He just chuckled and rolled his shoulders before tilting his head expectantly, as if waiting for an answer. You let your posture loosen and released a breath you didn’t quite realize you were holding. “Fine. He works for a firm out west dealing mainly in healthcare. TA has been trying to expand to the west coast, so I threw out my line.”
Harry’s brows lofted. “Wow. I never knew healthcare could be such an… engaging topic of conversation.”
His words were light, but you frowned in confusion. “What do you mean?”
“Nothing. Just…” His gaze dropped for half a second and it seemed like he reverted back to ten years ago before the air of confidence seemed to lift his feet off the ground. “You seemed to be getting along well over here. You know… laughing and smiling.”
You let out a snort and shook your head. “I should hope so. Half of my business deals hinge on conversations like that going well.”
Harry just dropped his head forward even more, as if incredulously. “Being likable is never something you’ve ever had to worry about with work. You know what I mean.”
Again, your forehead wrinkled in a frown as your lips twisted. “What? No. Huh? What you mean? What does that mean? What are you trying to say?”
For a moment Harry looked… nervous. But it quickly wiped from his face and he straightened up and focused his gaze behind you. “And for you a… Oh!” You turned. Randy returned with a glass in each hand — his own finger of brandy in one hand and your drink in the other. His eyes flickered between you and Harry before he awkwardly set both drinks on the table on your right in order to extend his hand with a smile. “Hi! I’m Randy. I work for Trilogy in Washington.”
Harry returned the gesture with an easy, lopsided smile and his right hand outstretched. “Harry Castillo, Castillo & Lynch.”
Randy’s eyes widened in the slightest. “Castillo? Wow, it’s so nice to meet you! You… You throw a hell of a party.”
Harry chuckled while shaking his hand. “I’m not allowed within a ten-foot radius of event planning, but I’ll be sure to pass the message along. Thank you.” They released their handshake. An almost awkward air fell over your shoulders but it was quickly dashed away as Harry stepped closer to Randy as if to be heard over the music. “So, she was just telling me that Trilogy specializes in healthcare. Tell me about that.”
Randy’s hands were active as he gave the same sort of company spiel that he’d given you just twenty minutes ago. The drinks he’d brought back sweat on the table. You shifted to grab your drink and brought the straw to your lips, drinking now reverted back to nerves as you watched Harry and Randy go back and forth for a few minutes. They were completely engaged with each other while you had suddenly shifted to be the third-wheel in the conversation. It was as if Randy had completely forgotten you existed.
“Sounds like you have a hell of a company,” Harry said with a smile. “Listen, Randy, we’re always looking to expand our business partners, especially on the west side.” His hand reached into his suit pocket, and your jaw dropped. No way he was about to… “We’d love to know more.”
Yes. That was absolutely Harry Castillo’s fucking businesscard extended between his fingertips. To Randy. To the company you had just connected with.
“Sounds great!” Randy exclaimed as he reached for his own card. “We’re well-established in the Northwest but we’ve been dying to make some East Coast connections.”
Harry took the business card identical to the one in your clutch with a nod. “Look forward to hearing from you.”
You could barely contain your scoff as you turned on your heel and left the vulture to continue preying on his—no, your target. That absolute prick. The nerve of him. You had never seen anything like that before from Harry. From others, sure. It could be a cutthroat world when networking off the books. The difference between a Fortune 500 company like Castillo & Lynch and a moderately successful company like TA Associates always came down to the connections made between other businesses. You had just talked to Harry about TA wanting to expand west, and now that’s suddenly that’s the direction his company is heading too?
You had never seen Harry and Castillo & Lynch being rivals, being that aggressive. It’s not like you were going around spilling company secrets and agendas willy-nilly, not like you were poking and prodding around for what his company’s next move would be in order to spoil it. But now it seems like you’d made a huge mistake by sharing your networking with your friend. Your closest friend, your longest friend. And now he’s just… betrayed you like that? Like it was nothing? Business as usual? You feel as if you had been taken back ten years to the year of radio silence when Harry abruptly went MIA.
Maybe sitting next to him at Columbia had been the worst decision of your life…
…
It took Harry five minutes to realize you had disappeared. Randy was good company as they chatted numbers and logistics and arranged for a future video call between the heads of Castillo & Lynch and Trilogy. By the time they grinned and shook hands one more time, you were long gone.
It took another thirty minutes to realize you were avoiding him.
He finally found you near the coat closet, arms crossed firmly over your chest as you waited in line.
“Leaving so soon?” Harry asked, startling you. You turned to look at him but your eyes quickly narrowed in a glare. “You know, we used to shut these things down back in the day.”
His attempt to make you even crack a smile failed pathetically. “Yeah, well, clearly things change.”
Harry frowned. “What’s that supposed to mean?” You rolled your eyes. He had never seen you like this before. Sure he’d known you were a hell of a businesswoman and could startle men enough to believe hell had frozen over with a single look. But Harry had never been on the receiving end of those looks. You turned to the coat clerk but Harry quickly wedged himself between the two of you. “Hey, wait. I’m serious. What’s… all this?”
You flipped your gaze to the ceiling as if you couldn’t believe what was happening — and you really couldn’t. How quickly he had changed… “Harry.” He only raised his eyebrows, silently begging you to continue. As if he truly had no idea why you were this perturbed. So with a sigh, you folded your arms across your chest once more. “I know for a fucking fact that Castillo & Lynch isn’t currently trying to break into the medical equipment field.”
His brows knit together even further, somehow simultaneously looking impossibly soft and ridiculously clueless. God, you could smack him. Or run your hands through his hair. “Right. We’re… not.”
Now you arched your brows almost to your hairline. “Yeah. You’re not.” Harry’s face didn’t move an inch. It seemed like he still didn’t get it. You threw your hands out in exasperation. “So why the fuck would you poach a potential business partner right out from under me?”
“Poach?”
“Yeah, Harry. Poach. You absolute dickhead.”
“That’s not… I wasn’t trying to poach him from you.”
“Oh really? Then what the hell was that back there?”
“I…” Harry gaped for a moment as if searching for the words. “I was networking. Making connections with potential future partners. Just like every other person in this ballroom. Don’t act like you don’t know how it goes.”
Your glare turned to ice as he belittled you. He seemed to realize his mistake as soon as the words left his mouth but he couldn’t take them back. “Oh, I know how it goes. I also know that you’re my friend, and I trusted you.”
“Trusted?”
“I told you things. I shared what our plans were and who we were trying to connect with. You knew that TA Associates has been trying to broach into the healthcare field for months. And when I tell you that I’m finally making a connection that would help me with the promotion I’ve been dying for for years… You swoop right in and steal the connection I made.” You completely disregarded his attempts to try to butt in or defend his actions, your chest heaving in frustration with every sentence. “I know what kind of world it is, Harry. I know it will always come down to who you know and how strong you can present yourself and your business to partnerships. But I never thought that you’d try to sabotage my progress.”
“I would never try to sabotage you.” He looked offended at the accusation, at your words, at your frustration with him. Hurt flashed across his face. “And I never could sabotage you. You’re a… You’re the best in the boardrooms and in networking I’ve ever seen. You could talk someone out of their wallet before they even realized they’d given it to you.” Your cheeks burned. What? Now you were the one who felt confused. “And you weren’t talking business anymore.”
“What?”
“You’d already secured a meeting with Trilogy within… five minutes.”
“And?”
“And you were still talking to him for like twenty more minutes. And you were laughing and touching each other and getting drinks,” Harry rambled.
“So what? What does that have to do with you suddenly coming in and trying to work them into Castillo & Lynch?”
“I - I didn’t like… I didn’t… I…”He flushed and suddenly looked everywhere but you.
And suddenly, it all came crashing into your chest.
“Wait a minute… Are you jealous?”
Harry chuckled awkwardly as he scratched at the back of his neck. “Wh - What? I mean, come on…”
You laughed also, but this one came out cruel and disbelieving. “Are you serious? You tried to wreck my networking because you were jealous? What are you, twelve?”
Harry didn’t laugh. He just… watched you. You could see his brain processing and malfunctioning behind his eyes. And he looked… devastated. As if your words had reached out and physically struck his cheek. You quickly looked down and swallowed hard.
“I wasn’t… trying to…” He trailed off again before sighing. “I wasn’t trying to interfere. I just…”
“What were you trying to do then?” You asked, softer this time.
He paused for a long moment before finally speaking again. “I don’t know. I don’t know what I was trying to do there. I just… really didn’t like how I felt when I saw he was still talking to you. And you were just laughing with him. I - I don’t know.”
His words shook you to your very core. “You didn’t like how you felt… watching me be happy?”
“N - No! That’s not - That’s not what I meant.”
“You didn’t like seeing me laugh with someone else?” He shifted on his feet and bit his cheek. Again, you let out an incredulous snort. “No. No. You don’t get to do that. Not after all these years. Not now.”
“Now?”
“Yes, Harry. Now.” You shook your head and raked your fingers through your hair. Everything felt so muddy and flat out complicated now. “Do you have any idea how ridiculous this is? I have been by your side for seventeen years. I have been there for you and stood by you and watched as you shrunk yourself in every room you walked into. Then you disappeared for a year. And you came back taller and richer and more confident.” He froze. “And now you’re just… expecting everything to be normal now. And the one time — the one time — someone shows an iota of interest in me as a businesswoman and maybe even as a person, you just, you swoop in.”
Harry was quiet for a moment, and he swallowed hard. “You knew?”
…
You had stayed with his family company for fifteen months before finally landing a job with TA Associates based in Boston. It was in the months following your departure that Harry became… distant. Sure, you had moved to a different state and were no longer working for the same business so it was expected that you wouldn’t be as close as you were before, but Harry had made the effort of staying in touch those first few weeks. Then it was as if he had suddenly gone off the grid overnight. Calls missed, texts ignored, emails returned with an automated response: “Out of Office — Returning Nov 2017. Please use the link to schedule a phone call or Skype meeting.” You even stopped by his parent’s house on the 4th of July under the impression of spending the holiday with the Castillos as you had for the last seven years. They sympathetically informed you that both Harry and Peter were recovering from emergency surgeries and cancelled the holiday festivities for the year. However, your request to visit and check on them and offer help in any way you could was quickly declined and you were pushed away without fanfare.
To say you were feeling hurt and even the slightest bit petty was an understatement. Medical emergencies were understandable of course. But almost a full year without any acknowledgement of your existence, any attempt to respond, any inkling of a desire to continue your friendship had left a sour taste in your mouth.
So when Harry knocked on your door with a bouquet of flowers one October evening, it should have come as little surprise to him when you shut the door in his face. You were hurt. Maybe you weren’t best friends any more, but you thought you were still friendly enough that he could pick up the phone and open some form of communication. A quick phone call. A short abbreviated text. A formal email. A letter. Anything that would give some hint of an explanation of why he was being such a shitty friend. But no — all you’d received was fifty weeks of radio silence and a bunch of carefully arranged flowers.
Only through the locked door did Harry finally give his explanation: there was an emergency health episode and he’d undergone immediate surgery and intensive recovery and therapy lasting eleven months. Peter experienced something similar — not quite the exact same situation and diagnosis — and so his family and the company had been scrambling for the last year. It was a long, scary process, but he had fully recovered. And yes, he saw all the messages you’d sent. They made his day again and again and he wanted to share his gratitude in person as soon as he was cleared. Okay, way to set the guilt trip into motion…
When you opened the door and welcomed him into your apartment, the first thing you noticed was how much taller he was. A year was a long time, sure, and you couldn’t confidently say what his exact height was before, but it certainly wasn’t this. Now you had to tilt your head back to meet his eyes. He wasn’t short by any means before, but you know you for sure didn’t have to crane back to make eye contact. Did you bring this up to Harry? Of course not. He just shared he’d been through a traumatic year but he was here now and he wanted to see you and resume your friendship. You really didn’t think anything of it — perhaps he’d just gone through a late growth spurt. Not unheard of by any means.
But when you finally did return to the Castillo home in New York for an extended friends and family get together, you noticed Peter was also taller. Significantly so. And one late night internet search spiral later, you formed your theory of what had really happened: Harry and Peter had undergone leg extension surgery. $200,000. Up to a year in recovery. Expensive. Painful. Dangerous. Risk. Unnecessary. So fucking unnecessary. A year of radio silence from the Castillo family for what? A couple of inches?
Of course this was never brought up with either of them. It was only a hunch, after all. A well substantiated hunch with several “coincidences” aligning to point in the direction of that being the truth. But if your hunch was somehow incorrect and you did bring it up with the Castillos, then you’d be the dick. Accusing two wealthy financiers of undergoing a ridiculous cosmetic surgery when in reality they’d experienced sudden and traumatic medical emergencies, as they said, and hit their final growth spurt as late bloomers.
It always prickled under your skin, though. Especially in how Harry seemed different after being AWOL for a year. Much more confident in rooms with colleagues and business partners and rivals. Arrogant, even. Not cocky, not loud, not abrasive. But almost… fully evolved, in a sense. He’d always been a brilliant businessman. Just the right amount of complimentary, the perfect dosage of ass-kissing and sucking up, always quick on his feet with numbers and offers and counter-offers, charismatic as all hell, persuasive as they come. But before it was as if he second-guessed himself in the room where people were significantly above him. Bashful, shy, self-deprecative. Now, though, now he initiated handshakes and maintained eye contact and clapped shoulders with ease and confidence.
Almost as if those extra inches were intentional and implemented with a purpose. Ten years later and you still didn’t know if you were right. But now…
…
“Knew?” Your brows scrunched in confusion as to what part he's stuck on, but you quickly realized… “Harry…” you said softly, almost pitifully. “Did you really think I didn't notice?”
“You never… You never said anything. For all those years you never even hinted that you had an idea.”
You snorted. “I didn’t think you’d want someone to call you out on it. But yes, Harry, of course I knew. And of course after that women were throwing themselves at you. But I never tried to sabotage any of that. No matter how much…”
“How much you what?” Harry suddenly looked alive. Whereas before he was hunched more like a kicked puppy, now he seemed rejuvenated. Energized. Awake. Alert. Intent. “How much you what?”
Now it was your turn for your cheeks to flush as you cleared your throat. “It’s… not important.”
“I never wanted any of them,” Harry said bluntly, cutting you off. You frowned. “Those… women. Who threw themselves at me. I didn’t want any of them.”
You swallowed hard. Took a step forward. “What did you want then?”
He didn’t answer. Couldn’t, maybe. “Harry…” His eyes stayed firmly fixed on yours. And they softened so gently that your breath hitched. “Why didn’t you do anything then?”
He shrugged half-heartedly, shaking his head. “I… I don’t know. I was scared?” He laughed once, humorlessly, as you arched a singular brow. “And then too much time passed. And then it felt stupid. And then it felt impossible.”
You arched a singular brow. “Seventeen years is a long time to be scared.”
“I know. And… You’re right. I was acting childish. That was so far from the way I should have gone about that.” He again scratched at the back of his neck and blew his lips. “I’m sorry.”
You paused, mouth quirking slightly. “It’s not okay.” He nodded. “Like, seriously. Please don’t ever pull that shit again.”
“Understood.” Then his lips twitched. “So… what should I do, hypothetically, if I were to, say… feel jealous again? You know, in a non-twelve year old hypothetical way?”
“How about…” You stepped forward and straightened his crooked tie. “Next time… you tell me you’re jealous before you start stealing my networking contacts? You know, just to make sure we’re on the same page?”
Harry grinned now. He grasped onto your wrists as they hovered above his tie. Your name fell out of his lips softly. “I’ve liked you for a very long time. And I’d like to stop pretending you’re just a friend to me.”
“Yeah?”
“Yeah. And I’d like to take you out to dinner.”
Butterflies surged into your throat and you shivered slightly while holding his gaze. “Harry, I’d love to.” His entire expression relaxed and his eyes lit up. “After you call Randy and withdraw Castillo & Lynch’s invitation to a meeting.”
