No. You had no intention of telling Oliver about you and Malcolm. Not only was it something you didn’t know how to bring up, but it was also something that maybe your baby brother didn’t need to know about just yet.

Your gaze fell to your left hand where the diamond ring sat. Malcolm had proposed only a few months earlier during a three-week business trip in France for a joint Queen Consolidated and Merlyn Global business deal. Since then, neither of you had spoken about setting a date or anything to do with a wedding ceremony. A part of you was nervous to bring it up; you didn’t want to make Malcolm feel pressured and didn’t want to somehow, accidentally, bring up memories that would sadden him or anger him by reminding him of Tommy’s mother. The other part of you was nervous to bring it up to Malcolm because…because you weren’t sure you wanted to be married to Malcolm Merlyn. Not right now. Not with Oliver being alive and home and all those suspicions about Malcolm being involved with the Gambit bringing up not anger but dread.

You couldn’t imagine what would happen if that box got opened. You weren’t sure you wanted an answer to whether Malcolm had a hand in your family’s yacht going down.

“Oliver doesn’t need to know about my love life, Thea. There is no reason he needs to be told. Besides, it is probably best that we don’t overwhelm him too much. It’s like…how Mom wants to not bother Oliver with her and Walter just yet. Oliver needs time to settle and adjust. No doubt, he’s hardly at any time to mourn dad or…or even Sara.”

Thea nodded as you spoke and then rolled her eyes saying, “So, you’re scared to tell him?”

“Terrified.”

How could you not be?

Oliver from five years ago had been an asshole, but he still tried to fight every boyfriend you had ever had.

The last thing you needed was Oliver trying to fight Malcolm the moment he got back to Starling City, not to mention the awkwardness that could pop up between Oliver and Tommy as a result.

Sighing, you stood and brushed a hand through your hair while saying, “Look, I promise that I will tell Oliver, but for tonight lets keep that between us.”

“Us and Tommy, mom and Walter, Raisa, most of Starling City, and…” Thea continued as the two of you walked out from her room and headed downstairs.

She wasn’t wrong. Too many people knew and too many people could let it slip to your brother. But if you were being honest, your biggest concern was Moira. She hadn’t budged even a little on her dissatisfaction toward your relationship with Malcolm, and Moira took every opportunity she could find to try and keep the two of you apart. Even with you now living in Malcolm’s home.

It had been amusing at first, then weird, and then frustrating. It was like there was something she was trying to tell you without telling you.

Like Moira knew something about Malcolm she wanted you to know but couldn’t bring herself to spell it out.

“Tommy!” Thea grinned as she bounded down the last few steps and practically skipped over to where Tommy and Oliver stood, reconnecting in the entryway.

You met the gaze of your brother’s best friend (who just happened to be your fiancé’s son as well) and forced an awkward smile as Tommy greeted Thea. The two of you were on good enough terms, but you also knew each other’s secrets – secrets that neither of you wanted Oliver to know about just yet. It made the situation uncomfortable, and you were kicking yourself for not having spoken openly about it with Tommy before this dinner.

“Well, this is a sight that I have missed.” You finally spoke up, plastering a smile on your lips as you closed the gap between yourself and the others. “And to think Starling City was only just beginning to heal from the terror of Oliver Queen and Thomas Merlyn.”

Most of Starling City probably didn’t care that Oliver had returned. Those who were excited were, of course, your family and Oliver’s party friends.

Still, the thought of having Oliver home meant that there was a chance for some semblance of the familiar. As close to the “good old times” that you could get to with your dad being gone.

“We will try not to do anything too crazy.” Oliver smiled. His voice soft. He sounded sincere, like he truly had zero intention of being his old self, and his eyes held a softness that younger Oliver would have never shown – it would have ruined his party boy persona.

“Make sure you don’t.” you laughed as Risa stepped into the hall announcing that dinner was about to be served.

Thea snorted, “Let’s not keep mom waiting.”

Oliver chuckled at your sister’s attitude and wrapped an arm around her shoulders, teasing Thea about “Making mom happy” as they followed after Risa.

You couldn’t help but chuckle knowing that your stepmother or Walter had sent Risa to “collect” the four of you; no doubt, Moira was having flashbacks from your childhood to when you, Oliver, and Thea would get so caught up in something the three of you had chosen to do together that it would take your father coming home and being “stern” for the three of you to finally come back to reality.

The thought was bittersweet, but you didn’t mind it. You appreciated that you could remember things like that. Over the past five years, there had been plenty of days where memories of your brother and father had been the only thing that helped you get out of bed and get on with your life.

“Hey Y/n,” Tommy hissed, grabbing your arm, and stopping you from following after your brother and sister. He waited for the two of them to be out of earshot before saying, “Listen I just…wanted to make sure we were on the same page about…things. Like, what gets told to Oliver and what can be saved for some other time.”

You knew what he was talking about, and it had nothing to do with you and Malcolm.

It was kind of sweet that Tommy was so concerned about telling Oliver certain things because he wasn’t sure how his lifelong friend would react. It spoke volumes on how much Tommy respected and cherished his friendship with your baby brother.

You whispered his name and offered a small smile as your gaze slipped to your left hand and the diamond engagement ring that sat there. The smart thing would be to remove the ring altogether. After all, if Oliver didn’t see the ring, then he couldn’t ask about it, but you didn’t want to give the impression that you were ashamed of Malcolm and that you wanted to hide your relationship with him.

“I promise that I won’t say anything to Oliver about what you’ve been up to the last five years as long as you don’t say anything about me and your father. I just...I haven’t figured out how to tell Oliver about us yet.”

Tommy stared at you for a long moment, taking in what you had said, and then breathed a sigh of relief and nodded. “Alright, alright. Thank you, Y/n. I…thank you.”

“Any time, Tommy.” And you moved into the dining room to join the others.

While Tommy and Thea sat to either side of Oliver, you chose to sit across from Walter placing Moira (and Oliver) at the head of the table. You didn’t mind as it gave you a chance to speak softly to your stepmother and Walter about Queen Consolidated and it gave Thea the chance to soak up as much of Oliver’s attention and closeness as she desired. Thea needed that. She had been only thirteen when the Gambit went down – life was hard enough for Thea with being in her early teens, the loss of your father and brother hadn’t helped things at all.

Besides, you would have plenty of time to catch up with Oliver.

It isn’t like he’s going anywhere any time soon.

“…I was hoping to swing by the office.” Oliver’s voice pulled you out of your thoughts and you quickly snapped your full attention in his direction.

“Queen Consolidated?” you laughed, interrupting whatever Walter had been saying as a response to your brother. “You want to go to…how hard did you hit your head while on that island?” you teased while lifting your glass of wine to your lips.

“I had a lot of time to think while I was away.” Oliver smiled, although it didn’t reach his eyes. “I need something to do with my time, and I was thinking, why not make that something the family business?” his blue eyes looked from you to your mother and then back on you, “Unless this is your way of saying you want the company all to yourself?”

“Shut up, brat.” You laughed with a playful roll of your eyes, “I think it’s a brilliant idea for you to have a hand in Queen Consolidated. Dad would want it.”

“Then it’s settled.” Moira was beaming, clearly happy that Oliver had matured enough to show an interest in your family’s business.

You were proud of Oliver as well, but you couldn’t help but wonder what exactly had motivated your baby brother to want to take an active role in Queen Consolidated. Surely, most people who came back from the dead would want to take some time to rest and readjust to life. But Oliver didn’t seem to want to do that.

Actually, that look on his face…it’s determination. He’s home and he has a list of things he plans to do.

But what?

What has happened to you, Olive?

*

When you were younger, the thing you feared the most was that your baby brother and sister would hate you. That they would grow up and realize how lame you were, and they would then want nothing to do with you.

That morning when you got that call that the Queen’s Gambit had gone down, that your father and brother were lost at sea and presumed dead, you felt so silly for your childhood fears. You knew then that the worst thing imaginable was having those you loved ripped away from you in a moment, in the blink of an eye, without warning.

And now, standing outside with Oliver and avoiding going home to an empty house, you felt that fear in your stomach. Like this was all a dream and that you would wake up, having imagined Oliver being alive, and you would be back in that cold, dark world where your baby brother was gone. Taken from you by fate? A tragic accident at sea? Or…at the hands of unknown enemies.

“So,” Oliver sighed, turning to you with a smile, “When do I get to meet the person who gave you that?” he gestured toward crossed arms, at your engagement ring.

“The wedding?” you shrugged, trying to play it cool at first as you looked anywhere but at him. “It…the engagement is actually pretty new. We don’t have a set date yet.”

“Does mom disapprove?” Oliver asked the question softly, his gaze locked on you so tenderly.

You snorted, “Of course she does. Mom…doesn’t think he’s good enough or me. Which is crazy because he’s a businessman, he’s very successful, and his company actually has a lot of dealings with Queen Consolidated.” Your amusement turned to frustration as you spoke, frowning at your own words and the reminder that Moira could pop off and spill the beans about you and Malcolm at any moment.

“Do I know him?”

Your cheeks flushed at his question, and you found yourself chewing on your bottom lip instead of answering.

Humming, Oliver nodded and leaned toward you, placing a kiss to the side of your head as a sleek, black limo pulled up. “I know that I don’t have to worry about you, Y/n. You’re the smartest out of us all. If you’re sure enough about this guy to marry him, then I will trust you and try to wait patiently for you to introduce me to him.”

“Ollie.” You murmured, eyes filling with tears as you wrapped your arms around him, tucking your face into his shoulder as he returned the hug. “I fucking missed you, Oliver.”

He nodded in agreement, saying “I missed you too, Y/n.”

It took all you had to pull away from him, and it was only after the two of you had agreed to see each other again tomorrow that you finally forced yourself to move away from your baby brother and walk to the limo and Malcolm’s driver.

“Jude.” You nodded, refusing to show your surprise as you stepped past him.

“Miss Queen.” He greeted you with a tilt of his head and a small smile.

Smiling in return, you waved goodbye to Oliver once more before climbing into the limo and letting the door shut behind you.

It was only after you were off your family’s property and Oliver was out of sight that you looked beside you at the man who was supposed to be overseas.

“Darling.” Malcolm hummed, his lips turning upward into that ridiculously charming, crooked smile of his.

“You said…”

Leaning toward you, Malcolm placed a kiss to your lips while murmuring, “You needed me here more.”

Tears prickling in the corner of your eyes, you forced a breathless laugh and pulled away, settling back into the seat. “Thank you, Malcolm.”

“Of course.” He took your hand, placing a kiss to your knuckles, and set it in his lap – seemingly mindlessly playing with the band on your ring finger as he turned to stare out the window, watching the world fly by.

Content and exhausted from the day, you rested your head on his shoulder and let yourself drift off to sleep listening to whatever jazz number Malcolm had chosen for the drive.

*

I hope you all enjoyed it! And I hope you’re all a sucker for sister!reader x Oliver content as I am lol (Oliver being a brother is so lovely to me 😉 )

The next installment will be reader x Malcolm! Probably a gentle day for them! It won’t be out in the next two weeks as I have other one shots (non-Arrowverse) that I want to finish writing/editing/etcetera.

As always, if you want to show some love, feel free to sent me things through my inbox and I also have a Kofi if you would like to support me in that way!

Please be safe and I hope you are having a good day!

The two of you had been chasing each other for years. Nyssa’s entire life had been being the Heir to the Demon. Your life had been taking down Ra’s and his merry little band of assassins. It was only after Nyssa helped Oliver Queen stop Star City from being destroyed, did the two of you finally join forces. There was nothing for her to be the heir of and you were suddenly in the need of another purpose. 

“Nyssa, where are we going?” You peeked over the ledge of the building where you were hiding out on, waiting for Nyssa. There was another voice there, one that you didn’t recognize. Walking beside Nyssa was another woman, one that Nyssa knew well, but didn’t completely trust. They walked side by side, but you could see a weapon strapped to Nyssa’s side. 

“I have someone to meet,” Nyssa said and the other woman huffed. You took the opportunity while Nyssa wasn’t looking forward to drop down in front of her. “Y/n, this is my sister Talia. Talia, this is Y/n.” 

“Should I leave the two of you?” Talia asked and Nyssa gave her a curt nod. Talia subtly waved towards you and then walked away, leaving you alone with Nyssa. 

“She’s my sister, you need not worry,” Nyssa informed you. You laced your hand in hers and the two of you started walking towards the building where you’d been holed up the past couple of weeks. “I did not see you at the service today.” 

“You saw me at some point, didn’t you?” you asked Nyssa. She had made the arrangements less than an hour after Oliver’s funeral had ended to come and see you. 

“After everybody else had left. You would have been welcome there Y/n,” Nyssa told you. You didn’t doubt that, they’d all been your friends, but you didn’t feel right about how you had left things with everybody, including Nyssa. “I forgive you. Oliver had forgiven you Y/n. Why can’t you forgive yourself?” 

“Because when I look in the mirror, my reflection is covered in blood. I thought I was noble for so long, but I was just a killer. I took people’s lives and I didn’t think twice about it. How can you look at me and not see a monster?” 

“I don’t know if it’s such a good idea to drop it like a bomb... shouldn’t we just wait a bit?”

“Babe, don’t worry. All that matters to him is if i’m happy, and, well, you make me the happiest girl...so I think he’ll take it well.” Laurel tightened her grip on Y/N’s arm and squeezed her girlfriend’s hand, leaning into her. “And wait for what? Till he finds out himself? I don’t think he’d appreciate that very much.”

Y/N sighed, forgetting how close she was with her father. No matter the respect she held for Quentin Lance, he could still scare her to death whenever he was in ‘papa bear’ mode. “Yeah, but Laurel— are you sure? I don’t want to ruin-” 

Laurel shrugged and knocked on the door of her father’s apartment, “You aren’t just a temporary thing, Y/N. I am one hundred percent sure.” She sent Y/N one of her heartwarming smiles, making Y/N’s stomach fill with joy and love.

Quentin Lance opened the door and smiled widely and planted a kiss on his daughter’s head as she passed him to walk inside. His smile wavered a bit when he looked at Y/N. Her face resembled that of one of the Queen’s and thus of the man that indirectly took his other daughter from him. 

He forced a smile and quickly looked away from her, which didn’t go unnoticed by the two women. Laurel bit her lip, not knowing how to stop his hatred towards the Queen family. Sure, they hadn’t always done the right things, especially not when it came to the Lance family, but Y/N had never been a part of any of that. She didn’t deserve to be seen like one of them.

He quickly glanced between the two, curious as to why Y/N was here too but he decided to keep quiet. 

“Everything going alright with the case?” 

Laurel gave him a tight-lipped smile and put her hands in her pockets, “Yeah, don’t worry about it, dad.”

“Oh! I just thought you might’ve needed some insight on a case... or that you got some news...since...” He gestured to Y/N, in his eyes Laurel’s coworker, who was still standing awkwardly by the door. 

“Actually...” Before she continued, her eyes met Y/N’s to see if she still felt comfortable enough. When Y/N nodded softly, she walked over to her, grabbed her hand to lead her over to the living room and then motioned her dad to do the same. “We do have some news.”

Quentin raised his eyebrows in surprise and slowly sat down on the couch. 

“You got the judges on your side already?” 

He looked at the two women in expectation. 

“Well? What is it?”

Laurel looked at the woman next to her and immediately smiled at how one look into her girlfriend’s eyes could calm her down. She felt Y/N slowly trail her hand down her underarm before their fingers tangled together. Laurel sighed in content as she looked at their intertwined hands and brought them to her lips to plant a soft kiss on the back of Y/N’s hand. 

Quentin furrowed his eyebrows, putting two and two together— the lovestruck look on his daughter’s face confirming his presumption. He opened and closed his mouth, looking away.

“Wait, so- you two...” He gestured between the two women, earning two nods in return. He rubbed his chin, taking his time to let this sink in. 

Laurel’s previous calm state turned to one of worry when she saw the scowl form on her father’s face. 

“Laurel, I love you, but the choices you make in your dating life are awful.” He rubbed his temples and stood up. 

Laurel shared a worried look with Y/N before stepping up to him. “Dad! She treats me so well and no one has ever made me feel this happy, why should it matter if she’s a guy or a girl I-”

“Oh, for God’s sake, Laurel, I don’t care that she’s a girl. You could date a frog and I’d still be accepting of it but...” He took a deep breath, took a few steps through the living room before turning back around. “...a Queen?!”

Laurel crossed her arms and scoffed, “So that’s what this is about? I should’ve known you would never let your vendetta against them go.”

“That family has caused us so much harm. Did you forget that she shares the same DNA of the same guy who broke your heart... what? How many times? You finally dodged a bullet with Oliver...You never learn, do you?” He cocked his head to the side. Even though his words were harsh, his eyes were soft and filled with worry.

“Y/N isn’t anything like Oliver. You’ll see soon, if you just give her a chance.”

“Every Queen in that family has been involved with some really questionable stuff, Laurel. Oliver lied to your face so whose to say she isn’t as well?” He pointed a finger at the girl standing behind Laurel but Laurel immediately slapped it away. Her eyebrows now furrowed in anger instead of worry.

“Swallow your pride for once... if not for her... do it for me!”

Y/N slowly grabbed onto the fabric of Laurel’s sweater, nudging her backwards. She hated to see the two fight, especially over her. But Laurel didn’t move a muscle and kept staring into the eyes of her father, trying to get through his head. 

Quentin slowly looked at the woman behind his daughter— Y/N’s gaze fixed on her shoes. His face softened a bit at the sight as he immediately thought back of all the times he had seen her. Laurel was right— he hadn’t really ever heard any bad news of this Queen family member. Then he recalled the many hours Laurel had spent cooped up in her bedroom, crying over whatever had happened all those times with Oliver and all the danger they indirectly put his daughters through— and his expression hardened again. 

“Laurel- I-I’m sorry... That’s an unreasonable thing to ask of me. I want the best for you and I.... just don’t see her being that for you.”

Laurel widened her eyes and let out a shaky breath before a sneer appeared on her face. 

“I don’t know what you expected to happen but if you thought I would leave her because you don’t like her, you couldn’t be more wrong.” She started softly, “I’ve never...ever, been so disappointed by someone in my whole life, and that says a lot.” Her voice was slow and soft but her tone sent a shiver down Quentin’s spine.

“Well then, lucky for you, you have a best friend that has come up with the perfect plan to sneak you out of the house.”

“No.”

“Yes.”

“Absolutely not.”

“Pleeaassseee.”

“My father will kill me.”

“I’ll buy you a burrito.”

“Fine. But if my Dad catches me, your ass is going to be in the fire with mine too.”

“Deal.”

-

Oliver walked into the lair, where Diggle and Felicity awaited him. He strode towards them and crossed his arms. “What do we have tonight?” Felicity looked, nervous, and looked at Diggle before facing Oliver again.

“You aren’t going to like this.” Oliver’s arms dropped, and he began to feel uneasy.

“What?” Diggle sighed and rubbed a hand over his face.

“We need you to shut down this high school party.”

Oliver felt confused. Why was the Green Arrow running around to shut down some teenager’s drunken fun? That could be left up to the cops.

“Well, one of your enemies has eyes on the party. He’s hoping to do a hostage situation. There’s going to be a lot of rich kids there. He wants his vengeance on the elites of the city, and their kids are the way to do that. If we go and get the party shut down, he’ll have to run.”

Oliver nodded. “Sounds like we’ve gotta go bust a few teenagers.”

Diggle sighed. “There’s more.” Oliver raised his eyebrows. “(Y/N)’s there.”

“What?”

“I got the notification from the cameras earlier and saw that she snuck out. Figured I could tell you when you came in. Didn’t realize what she was doing, till the tracker on her phone alerted me she was at the party.”

“Fuck.”

“We need to get her out of there. If he realizes who she is-”

“I think he already knows. There’s no way he wouldn’t.” Felicity said softly.

Oliver took a few deep breaths to quell his fears. “He knows. I don’t doubt that for a second. Her death will just be the icing on the cake.”

“Oliver…” Felicity said gently.

“Let’s get suited up then.”

Oliver would not take any chances on his daughter’s life. Not when she was the most important thing in his life.

-

Three hours and a few outfit changes later, you were successfully out of the house and on your way to the party. The idea of your Dad figuring out where you were was dreadful, and enough to make your stomach turn into knots. This was a terrible idea and you should not have come. Over the loud, pulsing music, you could feel your heart rate start to race, the longer you were here. Your best friend suddenly materialized, with a random boy from your school on her arm. She shoved a drink into your hand. “C’mon, live a little! Have a drink, dance with Josh!” You shook your head and pushed the drink back.

“No, I need to go.”

“(Y/N), you always do this. You never have fun, you never do anything for yourself. Your Dad controls and dictates your entire life, and you just let him! I will never understand it! You’re a teenager, you’re supposed to let loose and have fun! Make mistakes! God, I can’t deal with your moping and whining about it anymore!” By this point, Josh had awkwardly left.

“I’m not asking you to!”

“Then fine! If this is how you wanna live your life, then I can’t be apart of it anymore.” She stormed off and you slid down the wall to a sitting position. You put your head in your hands failing to blink back tears. Suddenly, the lights went out and the music went silent. There was muttering around you until a figure began to emerge in the crowd. For a moment, you began to feel scared, until you recognized the figure. Shit.

“You all need to leave. You are all in danger. Now. Go! Go!” Oliver yelled and kids scattered around you until the building was empty. You heard two sets of footsteps head towards you and looked up to see Diggle and your Dad.

“Hi Diggle. Dad.” You mumbled, well aware of the fact that the tear streaks were more than visible on your face.

“Party’s over.” Oliver said.

“Wow, I almost didn’t figure that out.” Oliver rolled his eyes. “I mean, you couldn’t even let me come to a party. Oh no, you just had to shut it down and ruined all my fun.”

“You don’t look like you’re having fun.” You rolled your eyes and chuckled.

“Oh my god…” You muttered.

“We can finish this conversation at the lair. Right now, we need to get you out of here.” Diggle interrupted.

“Whatever.” you said, standing up and pushing past the two.

-

Tension-filled silence filled the lair. Roy, Thea, Diggle, and Felicity awkwardly stood off to the side, while your Dad sat in a chair a few feet away from you. You stood across from your Dad with your arms crossed. Your Dad finally spoke. “I am so disappointed in you.”

You laughed despite the situation. “What’s new?” Oliver raised his eyebrows but you didn’t notice. “I get caught doing the same shit you did in school, the same shit I have never done before, and you get to say you’re disappointed in me. Un-fucking-believable.”

“Yes, I am disappointed in you for doing the same shit I did in school. Because I expect you to better.”

“What? You want me to not fuck up like you and have a kid you don’t give a shit about?!”

“Is that really-”

“No, I’m not fucking done!” Oliver sat back in his chair. “For once, in your god damn life, you are going to listen to what I have to say! You have been absent my whole life, and then you come back and you want to dictate what I do! And I understand, I understand a lot of that time wasn’t by your hand. Dad, I’m a fucking teenager! I’m going to fuck up! I’m going to make mistakes, just the same as you did! But you have to let me! I know what you do for this city, and I know why, but what does that shit have to do with me?! I want to have friends, and maybe a boyfriend, and go out, without Diggle or Thea or Roy with me! Let me be happy!” You began to feel out of control as you become more and more overwhelmed by your tears. “I am- so fucking tired- of feeling- not- enough. You didn’t- want me- I- know that-. But I can’t- do this- anymore.”

Oliver took a few deep breaths. “(Y/N), I was a nightmare teenager. And god only knows how much I drank when I slept with your mom. But I have never, ever, for a second, regretted having you. I am so disappointed in myself for making you feel that way. Before I disappeared, I knew that I would not be able to be a good parent to you. But when I was on that island, thinking of you was the only thing getting me through. I swore to myself I’d step up and protect you and be a good parent. I have seen a lot of vile acts and heinous people hurt so many in this city. And you are always one of their main targets. I could never, ever live with myself if you got killed because of my work. I can’t take that risk. That’s why we shut down that party tonight. One of my enemies had his eyes on you and that party. I could not let anything happen to you, or those kids.”

“Dad, I know you want me to be safe, but your need for me to be safe is overriding my ability to be happy. Please.” there was so much emotion behind that last word.