A/N: Warning everyone! I wrote this while I was buzzed on a bottle of red wine, but don't worry, I edited it while completely sober. All I'm saying is don't blame me entirely for the ridiculousness of this particular one-shot. Please, read and review!
(2/02/2016) A/N: This one-shot has actually been written for months but then I forgot about it. I only just recently rediscovered it on my computer and, after going through it again, decided to post it. However, this doesn't mean I am back to writing Olicity works, and this "What if?" collection will remain labeled COMPLETE. It is always lovely to hear from my readers, but please be aware that am not taking any requests at this time. I have two other works in progress for Bones and Charmed and any NEW fanfic writing will be devoted to those stories (though, a hectic life seems to be interfering with that at present). With that said, please feel free to read and review. Thank you!
Just Put a Ring on It Already
Why did purposing to the woman you love have to be so hard? And nerve wracking? And just flat out intimidating as hell? Because that's the kind of chaos that Oliver Queen deals with on a daily basis. You'd think he'd be used to it, but no. So, here he was thinking about how that night just a couple months ago he'd had everything planned out so perfectly and now he was struggling with the fact that he couldn't find the absolute perfect moment to purpose to one Felicity Smoak…again. Everything just seemed to constantly get in the way. First it was his sister, Thea and his ex, Laurel; then their return the Starling…no, Star City. Dhark showed up and caused trouble. He's still causing trouble as a matter of fact. Though, now they were all aware that he was Felicity's father, and boy, hadn't that been a revelation! The idea that someone so innocent and good as Felicity could come from someone so…well, dark was just unfathomable. Lord knows the day that had come out, which was about three weeks ago, had been the day that Oliver had been seriously worried about Felicity's emotional state. He had never seen her cry so much before and he honestly hadn't known what to do. At first he'd just held her in his arms, then he tried distracting her with sex – lots of sex – plus he'd bought her some new tech-toys for the lair. The list went on and on about the things he'd tried to comfort her with, and it had worked…for a while. It wasn't until two weeks after the revelation of Dhark being Felicity's father came out that he'd begged the Arrow Team for some kind of help. In the end, the entire Team had come over to his and Felicity's loft: Digg and Roy had helped him make a nice homemade dinner, meanwhile Thea – who had a lot of experience with psychopathic fathers – and Laurel – who had experience with family drama to the nines – along with a motherly Lyla had all crowded into the master bedroom and spent the day holding, talking, and comforting Felicity in a way that Oliver hadn't thought of. He hadn't realized that she just needed a woman to comfort her and remind her that her father didn't define her and that she had a brand new family already there for her.
As any outsider to the situation could see, things had complicated Oliver's plan when it came to purposing to Felicity. He just wanted that perfect moment, not because it mattered to him but, because Felicity was worth every perfect moment; she deserved perfect. So, there Oliver was, sitting in the new tech-ed-out Arrow Lair in one of the lone desk chairs around Felicity's computers moping around wondering if the universe had it out for him when who should walk in none other than Digg followed by Captain Lance, the latter being a bit weird for Oliver. He never thought what it would be like having Lance of all people wandering around his Arrow Lair.
"Hey man, what's up?" asked Digg as he spotted Oliver's overly brooding look as he glanced up to great him and Lance as the entered the Lair.
"Nothing," said Oliver despondently while he twirled something around with his fingers. A particular something that Digg quickly realized what looked to be a…
"What is that?" asked Lance as he too spotted the ring in Oliver's hand, his eyes widening in surprise. "Is that a…" The dark look that Oliver gave the pair of them silenced Lance's inquiry.
"Do you want to talk about it?" asked Digg as he took a seat. Lance hesitated in joining in but in the end his curiosity to whether or not Oliver would actual admit to the "engagement ring" he was fingering was just too much and he too took a seat across from Oliver next to Digg.
"What's there to talk about?" said Oliver hesitantly. He wasn't entirely sure he wanted to have this conversation with Lance around. Digg, he could probably buck up the courage to ask for some advice, but Lance? Yeah, that wasn't going to happen. But as Lance took his seat across from him, Oliver quickly realized that he just might get their helpful advice whether he liked it or not.
Digg gave a deep, exasperated sigh before he began speaking. "If that's an engagement ring like I think it is, and you undoubtedly plan on asking Felicity, my question is, why haven't you?"
"I just…haven't found the right…perfect moment," mumbled Oliver with a frustrated frown etched on his face.
This time it was Lance that heaved a heavy sigh. "Listen, every man is wasting time looking for the perfect moment to pop that question. The truth is there is no perfect moment in itself. The world is filled with imperfect moments," said Lance with a very serious look drawn across his face as he seemed to stare Oliver down. "We are the ones that have to make the moments perfect. You can't just spend your life waiting for them to just happen. Sometimes you need to give destiny a helping hand." With that, Lance got up and started to make his way out of the Lair before he stopped, "Oh, and Queen?" Oliver glanced at Lance while Digg just stared at the older man in wonder at his very sage advice. "The next time I see Ms. Smoak, she better have that ring on her finger." Oliver and Digg's brows both shot up at Lance's blatant blessing mixed threat. "Oh, could you let me know the next time Felicity's mom is in town?"
"Uh, yeah…why?" spluttered Oliver in confusion.
"Well, I didn't get the chance the ask Donna out for dinner the last time," said Lance matter-of-factly before he promptly left.
"Okay, now that that's all cleared up…whatever that was," said Digg. "Are you gonna go pop the question already?"
Oliver opened his mother to answer but before he could the Lair was intruded upon with Thea and Laurel's mutual entrances. Oliver did the only thing he could think of to ensure that his sister and ex wouldn't see the engagement ring and tossed it up in the air to Digg who caught it confusedly.
"What the hell am I supposed to do with it?" Diggle whispered urgently but Oliver's only response was to wave his hands around like a lunatic in an attempt to tell him to "kindly shut up."
"Uh…you guys ok?" asked Thea with a look of worry plastered on her beautiful face at her brother's seemingly crazy antics.
"A-hum…yup," said Oliver, not realizing he was giving Thea, Laurel, and Digg a blatantly terrified, wide eyed look.
"Digg, why are you holding an engagement ring behind your back?" asked Laurel. Digg hadn't realized she was standing right behind him when he'd done that.
"Umm…" was Digg's eloquent reply. And if things couldn't get worse, none other than Felicity Smoak, followed by Roy Harper – who was like a little lost puppy nipping at her heels – entered their lair. If it were possible, Oliver's eyes grew even wider.
"What's with the funny faces?" asked Felicity as she dropped her things on her desk before turning to look at the people around her. Her family was strange to begin with, but this seemed to be taking it to a new level. She turned to look at Oliver and would've given him her customary kiss but he, too was acting weird. "Guys…"
"Alright, you know what? I have spent the better part of three years refusing to get involved with your guys'…tension. I'm not breaking that streak now," said Digg as he promptly tossed the ring back at Oliver who, due to a slight state of shock, didn't catch it which allowed said ring to plonk him right on the nose before falling to the ground. "Just but a goddamn ring on it already, man!" With those last loving departing words, Digg raced out of the lair – grabbing Roy by the scruff of his neck and dragging him out with him.
Meanwhile, Laurel and Thea were busy looking slack jawed at the ring that sat idly at Oliver's feet. Thea was the first to move as she picked up a rather familiar looking diamond. "Hey, is this…"
"Mom's," finished Oliver. "Well, the center diamond is, at least. I-I, um…had it reset with the emeralds from our great-grandmother's ring.
Thea just nodded her head as she gazed down at her mother's diamond that now sat surrounded by small delicate emeralds on a platinum band. When she looked up, she caught Laurel frowning and for a second she thought the older woman would say or do something in regards to the engagement ring that Oliver would never give her. But, surprisingly, the shock on Laurel's face slowly melted away until she wore a crooked smile. When Laurel finally looked up from 'undoubtedly-Felicity's' engagement ring, there seemed to be a look of piece and…acceptance written across her face.
Laurel stepped forward to gently take the ring from Thea's fingers and placed it back on the floor before giving Oliver a conspiratorial wink before she turned to Thea. She placed her hands on the younger woman's shoulders and turned her towards the lair's exit. "Why don't we give these two a moment to sort things out," said Laurel before she and Thea also disappeared from sight just as Digg and Roy had, leaving Felicity and Oliver to stare down at the ring that was once again glinting back up at them from its spot on the floor.
Oliver knelt to pick the ring up, and just like that he understood what Lance had meant about making perfect moments. Oliver looked up at Felicity from his kneeling position just as she tore her wide surprised gaze from the ring to look at him. A slight, hopeful smile graced her plum-painted lips. "There's something I want to ask you. Something I've wanted to ask you for…a long while now," said Oliver, and just like that…everything was perfect.