Author's Note: Welcome to my Olicity Christmas AU! This is the story that I wrote during NaNoWriMo 2014, so its all finished and I'm just editing it now so the updates will be fairly regular. Note: THIS IS AU. Meaning this is not set during the canon-verse of the show. Same characters though, just no island for Oliver and no vigilante business. Sorry about that! This is also meant to be a bit cheesy: think Hallmark Channel Christmas Movie starring our favorite duo! I know, right? ITS TOO MUCH!
Oliver Queen had been avoiding his mother's phone calls all week long and he knew he'd used up his last credible avoidance the day before when he'd faked a last-minute emergency meeting with the shareholders. So when his assistant buzzed through to his office to tell him his mother was on line one, well, he knew his number was up. He told her he'd take it.
Reluctantly, Oliver turned away from the business reports he was reviewing on his oversized monitor and picked up the receiver on his office phone. "Oliver Queen," he said in greeting.
"It's about time you took my call," his mother's crisp voice replied. "If I didn't know any better I'd say you've been avoiding me."
Because that's exactly what he'd been doing and this was his mother's way of letting him know that she knew it. "I've been busy, Mother. You and Dad the ones who wanted me to take an interest in running Queen Consolidated. You've got your wish, or rather he did, but it doesn't afford me a lot of free time."
Any hope that his pointing this out would get her off his case disappeared with her next words. "No, you just don't want me to harass you about your father's will."
He cringed. Damn, that woman was too smart for his own good. "I'm not worried about it, Mother, and you shouldn't be either."
"Oh, does that mean you've found a woman to settle down with? Or have you patched things up with Laurel?"
"No, Laurel and I are still broken up," he admitted.
"There are less than six months now until your thirtieth birthday, you realize."
"Yes, I do realize that."
"I can set you up with someone, if that would help. You know Frank Bertinelli, right? His daughter, Helena, is a lovely young woman and she recently broke up with her fiancé so she's definitely available."
Oliver fought a shudder as he sat back in his chair. Helena Bertinelli was a train wreck. He remembered that from when they'd been at high school together. The last thing he wanted was to get sucked into her drama. As for Laurel, well, he considered his relationship with her to be a work in progress. Normally, he'd be happy to let it run its natural course, if it wasn't for his father's damned will. Ever since he and Laurel had begun dating back in high school, they'd had a tumultuous relationship that resulted in breakups and makeups. It was just a part of who they were as a couple. So he had every confidence that they would one day end up back together again. Unfortunately, he didn't have the luxury of waiting for that one day to arrive.
For the last seven years since his father's death, Oliver had done his best to ignore the elder Queen's last wishes. Growing up the son of billionaires, heir to a business empire that spanned the globe, he'd never worried about his future financial security. As such, he'd probably taken too much for granted. As a teenager and a young man, Oliver's life had been defined by the latest party, the latest drunken binge, the latest string of nameless women… He'd run fast and far from any hint of responsibility and for a while, things had been great.
But his father had grown tired of his antics the older he'd gotten and had on many occasion taken him aside for a lecture. Oliver had never listened, of course, and had gone on to flunk out of each university that his father bought him entry to. The weekend before his father had been lost at sea in a tragic yacht accident, they'd had a huge fight, their biggest yet. Robert had threatened to cut Oliver off unless he took responsibility for his life. Oliver had been furious at his father's lack of understanding and had stormed out of the mansion. What had followed had been a bender to end all benders, and with his best friend Tommy as his wingman, they'd gone from party to party to party. Finally, the pair had crashed back at Tommy's penthouse two days later and had slept for days. Oliver had eventually woken up to the mother of all hangovers and the news that his father's yacht had gone down somewhere in the North China sea.
The search for survivors had been called off a week later and plans for a funeral service had been taken over. The lawyers had contacted the family regarding Robert's will shortly after that and that was when Oliver had officially gotten his wake-up call. The will had clearly stated that Oliver would inherit an equal share of the estate when, and only when, he fulfilled certain terms which were outlined in great detail.
The first term had been: finish college. For as much flunking out as he'd done, Oliver only had about a year and a half of classes to make up in order to get a business degree. He took classes at Starling City University and managed to squeak through, with help from some professional tutors his mother hired to keep him in line. His relationship with Laurel had been on at the time and she had also provided much encouragement for him to make it through. Laurel was smart and beautiful and going places and why she kept giving him chances, he'd never know, but she did. She'd gotten her degree a few years earlier and was well on her way to passing the bar exam and becoming a successful lawyer.
The second term had been: take over as CEO of Queen Consolidated. In the interim, his father's CFO Walter Steele had filled in and kept the company afloat. For the first year after Oliver graduated, Walter stayed on board to guide Oliver and show him the ropes. Finally, three years after his father's death, Oliver took the reins of Queen Consolidated. Walter returned to his position as CFO and also started dating his mother. Oliver hadn't really been thrilled about that development, but he did like Walter and valued the man's sensible judgement so he'd been willing to overlook it. Besides, his younger sister Thea simply adored Walter and was thrilled to have a father figure in her life again. Seeing his sister so happy, when she hadn't really been happy since their father had died, had made it all worthwhile.
But then Walter and Moira had been married just three years ago and instead of taking the focus off of Oliver, it had only served to magnify it. Suddenly, the third term of his father's will became all his mother would talk about. That third term stated that he needed to be married by the time he turned thirty years old.
Oliver might have changed a lot about himself in the last seven years, but he doubted he would ever be the marrying kind. And the closer his thirtieth birthday drew and the more pressure that was heaped on his shoulders, the more reluctant he seemed to become about the whole thing, to the point he refused to discuss it with his mother.
When the will had first been read, Oliver had assumed he'd talk Laurel in to marrying him and that would be that. He'd known Laurel since high school and while they probably spent more time broken up than they did actually together, she was the closest thing to an actual girlfriend that he'd ever had. That was probably because she was the only woman who seemed to be willing to overlook all his indiscretions.
Oliver Queen often wondered if he lacked the ability to be faithful. He was also certain that faithlessness was a trait that ran in his family, as his father had notoriously had many affairs and hadn't been very good about hiding the evidence. Oliver didn't feel good about shackling any woman, much less one he cared about, into a marriage where he'd only bring infidelity and disappointment.
Despite all that, he'd come close six months ago. He and Laurel had been on again for the longest span of time yet: a whole year. Sure, he was busy with the company and often working late and she was busy working at the DA's office and they were more like ships passing in the night than anything else. He hadn't really had time to screw up the relationship. But, the fact was, he hadn't cheated on her and there'd been no huge fights and no tearfully slammed doors or anything of that sort. Oliver thought maybe he was finally growing up and outgrowing his inability to be in a stable relationship. But then, Laurel had suggested they move in together.
Just like that, Oliver had felt the prison doors slamming closed on him and he'd panicked. He'd panicked hard. Laurel's younger sister, Sara, had always been a good friend of his and they'd always flirted with one another but he'd always kept it innocent. He knew Sara was attracted to him and he was to her but it was a line he'd never crossed. That is, until that night six months ago. He'd called Sara up, wanting someone to talk to. He'd told himself he just wanted friendly advice about his relationship with Laurel. But when Sara had shown up at his door a half hour later, he'd grabbed her by the waist, yanked her to him and kissed her for all he was worth.
They'd gone at it like rabbits, all night long, and all the next day too. They only surfaced for the occasional (tandem) shower and food. Oliver had felt the blissful release from responsibility as anything outside of his loft apartment had ceased to exist over that one, glorious weekend.
It hadn't lasted, of course. Monday had arrived and both Sara and Oliver had a list of texts and missed calls on their phones from Laurel. When Laurel had stopped by QC to see him that morning, she'd already known. She was a smart woman, she'd figured it out. The two people she couldn't get ahold of, conveniently, all weekend long, suddenly reappeared on the radar at the same time. And, according to her, they each sported matching guilty expressions on their faces. There'd been no screaming this time, no throwing things, no slammed doors, just a cold declaration and the echo of her heels clicking on the marble tile as she'd stalked out of his office.
Laurel hadn't talked to him since, though he'd spoken to Sara several times and begged her for updates. Apparently, Laurel had only recently begun speaking to Sara again but only to let her know that yes, she was still furious with her younger sister.
It was stupid. This was the most terrible mistake he'd ever made. And now, with six months until the deadline in his father's will, Oliver had no idea what to do. His mother breathing down his neck about the whole thing was definitely unhelpful. She knew Laurel had broken up with him (again), but not why and he hoped to keep it that way.
"Setting me up with Helena won't be necessary," he told his mother, returning his thoughts to the conversation.
"But the deadline—"
"Yes, Mother, I know the deadline is looming," he sighed. "I've got it under control." His mind raced for a moment, hoping for something to tell her to keep her from continually pestering him about this. "I'm actually seeing someone seriously right now. She might be the one."
"Hmm, really?" She sounded skeptical. "Well, you know the holidays are upon us and I expect to see you at the family cabin to celebrate with us."
Oliver bit back a groan. "It had slipped my mind. I have been busy, you know."
"Oliver, you are not skipping Christmas with us this year. I won't allow it. Thea is counting on you being there and so am I. Plus, I'd like to meet this woman you're dating. I expect you to bring her along."
Oh, shit. "That's not a good idea, Mother. It's—"
"Nonsense. We'll all be up there on the 23rd, I expect to see you before dinner that night. You know where it is but in case it's also slipped your mind, I will send directions to your secretary to forward to you."
Shit, shit, shit. "Yes, Mother."
She rang off a moment later and Oliver set the phone back in the cradle. He stared at it for another minute before letting his eyes slide shut.
"Shit!" he cursed loudly. How the hell was he going to get out of this one?
By the next morning, Oliver had thought up a strategy. He'd been spending the last six months since Laurel had broken up with him waiting for her to be ready to take him back. Honestly, he'd expected her to come to him at least a couple of months ago. This was the longest she'd managed to stay mad with him, during all the years of their relationship.
Then again, he'd never cheated on her with her own sister before either. Even he knew that was above and beyond his usual douchebaggery. So maybe that meant he needed to step up his game and be the one to pursue her. That had never been his style and frankly, he'd never really had to before, but Oliver knew he was meant to be married to Laurel. She was the only viable choice for him. It was time he showed he was committed to the idea.
The first step in his strategy was to deliberately cross paths with Laurel and force a conversation. Maybe he would get lucky and all it would take is a heartfelt apology on his part and she'd consent to join him on this enforced family Christmas vacation. A guy could dream. He could make up some sort of excuse to his mother.
As soon as he got to his office, he called the DA's office. Instead of asking directly for Laurel, he asked for a paralegal named Sandy that he knew worked with her. Turning on the old Oliver Queen charm, he managed to finagle details about where Laurel was taking her lunch that day. The sandwich shop Sandy mentioned was just down the street from the DA's office and he knew right where it was.
When he hung up, he immediately placed another call. This time to his best friend, Tommy Merlyn. He'd known Tommy since they were both toddlers, having been thrown together because of being the eldest children of two of Starling City's most influential families. They'd been thick as thieves ever since.
"Hey Tommy," he greeted once his friend picked up. "Hey, I've got some bad news."
"Oh no, don't tell me. That bimbo you took home from the club last weekend has developed a sudden clinginess? Or… you've overshot the limit on your platinum card? No wait! You ran the Jaguar into a mailbox and now you've got to get body work done."
Oliver grinned. "None of those things. Don't I wish! I have to back out of Aruba."
"What?! Oliver, we've had those plans for ages! We were going to lay on the beach for five days straight and get pissed. And laid! Remember all the laid we were going to get?" Tommy cried, his dismay evident.
"I know. Trust me, I'd much rather be doing Aruba with you. But my mother…"
"Ugh. Say no more. I know better than to question the will of Moira Queen. Damn, Oliver, that blows. Does this mean I have to spend the holiday here in Starling? With my father?" Tommy's shudder was audible over the phone line.
If anyone's relationship with their father was more dysfunctional than Oliver's (while his dad was still alive, that is), it was Tommy's. That was why Oliver had suggested the trip to Aruba in the first place, to rescue his friend from having to deal with his difficult father over the holiday. Truth be told, the partying lifestyle wasn't so much Oliver's speed anymore and he suspected it wasn't Tommy's either. But a week on a tropical beach had sounded like just the thing and now…
"I'm really sorry, Tommy. I'll make it up to you, I swear. Maybe we can go somewhere for New Years."
"You're assuming I'm going to survive Christmas," Tommy grumbled.
"How about you and I go for drinks tonight. I'll tell you all about my troubles, hopefully they'll take your mind off yours," Oliver suggested.
"Oh hey, I like the sound of that!" He sounded happier already.
Later, as he walked to the sandwich shop which was just a few streets over from the Queen Consolidated building, Oliver thought again about his plan to win Laurel back. It had to work because Plan B was something he wasn't even willing to contemplate at the moment. That was simply a backup plan. An emergency clause. Chances were, he wouldn't even need it. After all, didn't he have charm on his side?
Oliver spotted Laurel as soon as he stepped into the crowded shop. She was standing in line back by the counter, waiting to place her order. Fixing his smile in place, he walked over and stood behind her. She didn't even notice him and he took the moment to look her over. He hadn't even seen her in months and heaven help him, he missed her.
Laurel had been a beautiful girl as a teenager and now, as a woman, she was flat-out stunning. Tall and willowy, with long, naturally waving brown hair that was currently cascading down her back, she could have been a runway model. She was wearing a sleek, cream colored suit that showed off the lean lines of her body and plenty of leg too. She carried herself like a woman who knew what she wanted and wasn't afraid to chase it down. He really admired that about her, always had.
Laurel was next up in line and she stepped to the counter. The employee asked her what she'd like and she'd just opened her mouth to answer when Oliver spoke up. "She'll take a 6" turkey, swiss and avocado on 7-grain bread, please. Hold the mayo, extra peppers."
Laurel whirled around, surprise written on her features. "Oliver! What are you doing here?"
"Was I right? That's still your favorite, right?"
She flushed, and her green eyes snapped with annoyance as she turned back to the employee behind the counter. "Yes, that's what I'll have. Thank you."
"I knew it. You've eaten the same sandwich for at least ten years."
Laurel kept her back to him as she moved along the sandwich production line. "It's actually fifteen years. What are you doing here, Oliver?" she asked.
"I was hoping to talk to you," he told her. He watched as her shoulders lifted in a sigh.
"I said everything I wanted to say to you six months ago."
"You were never going to talk to me again? Come on, Laurel…"
She whirled back around, her eyes snapping now. "Don't 'come on, Laurel', me! Yes, I was hoping I'd never see your face again. Guess that didn't work out for me though, did it? So I'll ask you again; why are you here?"
"Can we talk? Please?" he asked, dropping the charm and shooting for just being real with her. He hadn't anticipated she would still be this angry with him, after all this time.
She looked at him for a long moment, considering. Then, she nodded. "All right. Real quick though, I want to be able to enjoy my meal before I need to get back to work."
He resisted pumping his fist in the air in victory. If she was willing to listen to him, that was a huge step in the right direction. She wasn't as closed to him as he'd thought a moment ago. Oliver waited while she paid for her sandwich and followed her as she carried her tray to an empty table near the door. She sat heavily, not meeting his eye and he took the chair across from hers.
"Okay, so talk."
"Can't I just have wanted to see you, Laurel?" he asked.
She met his eye then. "I know you, Ollie. You wouldn't be here if you didn't want something. So spit it out."
"Well, I do want something. I want another chance with you."
Laurel scoffed loudly, causing a few people at the next table to look over at them curiously. Blushing a little, she leaned over the table towards him. "You really should have thought about that before you slept with my sister," she hissed.
"Laurel, please," he began.
She sat straight and narrowed her eyes. "Wait a minute. Is this about your father's will?" When he didn't reply, her eyes widened. "It is, isn't it? Oh, my god, Oliver. You just want to get back with me so, what, so you can inherit billions?"
More people were looking now and he ducked his head. "Laurel, quiet down. That's not the only reason."
"Oh, piss off, Ollie. I'm done with this. Get out of here so I can eat my lunch in peace." She started to unwrap her sandwich with jerky movements, signaling the conversation had come to an end. The women at the next table over were giving him accusatory glares and Oliver knew when he was beat. Dammit. He stood up and paused next to her chair.
"Call me if you change your mind," he said.
"I won't," she said simply.
Oliver sighed and walked out of the sandwich shop, tasting the bitterness of defeat. He decided he rather hated the flavor.
On his walk of shame back to the office, Oliver pulled his cell phone from his pocket and dialed Sara Lance's phone number. He'd spoken to her a few times since Laurel had broken it off with him and he still considered her a friend, though in the interest of hoping to win Laurel back, he'd kept their interactions to a minimum.
"Yello!" she called, answering as cheerfully as she often was.
"Sara! Hi, it's Oliver."
"Oh, boy. Are you ever on the shit list," she remarked, almost sounding gleeful about it. Oliver made a face.
"Did Laurel talk to you already?"
"Just got off with her actually. She told me, and I quote, to keep my boyfriend away from her. What the hell did you just do?"
"I'm not your boyfriend," he reminded her.
"Yeah, try telling her that. I sure have. Seriously though, what'd you do?"
"I ran into her at lunch, tried to talk to her. I told her I want another chance with her."
Sara groaned. "Ollie, she's not ready. She's still so angry about everything. She's barely talking to me, and I'm her sister."
"I know but—" He cut himself off. He didn't want to get into talking about the will. Laurel hadn't been entirely wrong about that and the knowledge ate at him a little. "Listen, can you talk to her for me?"
"And say what?"
"Just… tell her that I'm not a bad guy. I'm changing, I really am. See if you can get her to agree to talk to me. Please?"
She sighed and he felt guilty all over again. Sara might still have a crush on him, if she did she'd never said anything after their weekend together. If she did have feelings for him, asking her to talk him up to her sister was pretty callous but what other choice did he have? He hated to ask this of her but he was getting desperate. It wasn't just about the stupid Christmas holiday anymore. This was his life, his future. If he ever wanted to have something again with Laurel, now was the time to make it happen. Or forever hold his peace, as the saying went.
"I'll see what I can do. Dad's making us all do Christmas together this year. He doesn't like how we've been fighting this year. He blames you, you know."
"I know." And with good reason. Detective Quentin Lance wasn't exactly the sort of guy you wanted to be on the bad side of either. Oliver had gotten more parking tickets in the last six months than he'd ever gotten before in his life.
"I won't be easy, Ollie. She feels betrayed. But I'll talk to her."
"Thanks, Sara. That's all I can ask."
"If I don't talk to you before next week, have a great Christmas."
"Thanks, you too."
He hung up and slid the phone back in his pocket. He was outside Queen Consolidated now and he looked up at the huge steel and glass building with no small amount of trepidation. It looked like it was time for Plan B after all.
There was no chance that he'd get Laurel to come to the family cabin with him for the holiday now. And he had told his mother he was seeing someone new. This wasn't how he'd wanted this to go and god help him, if he had his choice he'd be going to Aruba with Tommy and not even considering doing what he was considering right now. Where he'd been feeling confident an hour before, now Oliver was filled with self doubt. He hoped that Plan B worked because there was no Plan C. No wait, that wasn't true. Plan C was Helena Bertinelli.
He fought off a shudder as he yanked the glass door open and strode through the open lobby to the bank of elevators. The hell with Plan C. Plan B had to work. He punched the button in the elevator car to take him to the fourth floor. It was time to pay a visit to Felicity Smoak.