So I really enjoy this master list of fics on makepatronusesnothorcruxes tumblr and I noticed there was a prompts page and one of the prompts was something about Betting and it sparked this so... yeah... now we're here.
Disclaimer: The actual show isn't mine, blah blah etc etc, you get how these things usually go.

"Twenty more on a month earlier" Digg called to Sara as he heard the door close, shutting out Oliver and Felicity. Sara was over by the mini-fridge shaking her head after the pair.
"I'll take that action, there's no way it'll happen before Christmas."
Digg tries to get her to budge, "you never know with all those festivities, all that cheer, all that… mistletoe."
Sara wasn't convinced, those two were impossible, "it's not magical Digg."
Digg turned back to fix her with a smirk. "No it isn't, it's a time for miracles."

Roy had been watch the remaining teammates banter after the Boss man and Blondie left. He though now's as good a time as any to actually figure out what they were talking about. "Am I missing something?"

Digg and Sara turned to him from the training mats. Sara looks back at Digg and then leans in with an over dramatic whisper, she asks Digg "should we tell him?"
Digg looks down at her and then looks back at Roy, "I don't know…"
"Tell me what?"
Diggle just continues as if Roy hadn't said a word. "He's already broke, I don't want to take all the kids money."
"Hey!"
Sara, unsurprisingly does the same as Digg, ignoring Roy she fixes Digg with a mock glare. "Think of it as a 'team bonding'thing." Shocking herself as she uses sarcastic air quotes. One too many girls nights with Felicity she thinks.

Digg caves, shrugging his agreement which results in both resident soldier and the Birdie turning to Roy and at the same time announcing, "We're betting on when Mum and Dad get it together."
If Roy actually got his mind around what they actually said, he'd register they're hilariously in-sync head tosses towards the door and then their simultaneous nods.

But instead, all Roy could get out was a, "What?"

Diggle jumps in first to explain, "You know, when Oliver finally pulls his head in and realises Felicity is the best thing for him"
Sara jumps in, "And who says she'll take him back straight away? Nope, I still think you're wrong Digg. It'll be New Years, she'll make him work for that New Year's Eve kiss." Leaving Digg to think about that, Sara turns to Roy, "You in kid?"

Looking between the overqualified bodyguard and Canary with confusion Roy wants to know the exact terms.
"I've got Oliver," Digg says "Sara's keeping an eye on Felicity; we'll know the minute they decide to get together."
Sara jumps in at this point and takes over for the details, the pool starts at $20 for the first bet and then anything over $20 there's a change of time seems fair enough as long as it's discussed with the team. Sara's great with numbers, but Digg has keeps a running count on his phone too, which seems fair enough. "It builds," she says and she challenges him "if you're feeling confident feel free to suggest upping your bet."

Roy thinks for a second, it was her job to explain not to confuse him more, but he thinks he gets the basics, the rest he guesses, they'll re-explain later. "Uhh… how bout I just put $20 on the night of the Queen's Christmas party that Thea's dragging me too and we go from there?"
Sara nods, "Okay, Digg you still good for Christmas?"
"Yup, still good for New Year's Eve?" Digg affirms.

All three team mates give a definitive nod before Diggle raises his staff again at Sara throwing a challenge at her with his raised eyebrow. At the same time you can hear skin resume slapping water from the other side of the foundry.

III

"Oliver Queen! Get back here! What do you think I am? A puppet? You can't just keep dragging me into a new department of QC like I'm dangling on a string hanging behind you!"
The team watch as Felicity tries to descend the stairs into the Arrow Cave as she affectionately calls it, fast enough to keep up with Oliver who's clearly trying to avoid the rapid fire hostility that are Felicity's words. She's pointing a stabbing finger at Oliver; she can actually be a little intimidating when she gets like this. Clearly she has full intentions to poke him, maybe it won't hurt her finger as much as it had last time. But she stumbles a little and has to drop her accusing finger to grasp the railing before she falls.

Oliver's waiting at the bottom of the stairs, Digg doesn't miss the fact that his brother in arms immediately turned and quickened his pace with his arms reaching back toward the bottom of the stairs when he heard her slip.

Felicity however doesn't walk down the whole way, Sara thinks it's for leverage, smart woman. This way Felicity holds him in place, locking onto his eyes. Oliver only lifts his shoulders.
"I need you there."

Felicity is the first to break away, releasing him to push past toward her computers in the main area of the lair. Roy rolls his eyes, he knows he's only new but he can tell this is a usual event considering the fact that Digg is less stoic and closer to chuckling and Sara looks like she's going to face palm with every line of Oliver and Felicity's banter.

Felicity turns back to Oliver mid stride. "For what!? You aren't the boss anymore and Mr Steele stepped in to take on QC and dropped you into Applied Sciences. What do you even know about Applied Sciences, you were stuck on an island for five years! You still have trouble keeping your phone updated!"
Again all she gets is an "I need you there with me."

Her blood boils, he doesn't understand. She's one acceptance away from being back with her babies in IT. "You need me there? To what, book appointments? Oliver, Walter's offering me a management position in IT. You need me there or you just want me there?"

For a second Oliver's face twitches, its super-fast and they would've missed its significance if not for his next words. "I want you there."

Felicity pauses for a minute. "Don't expect coffee. The machine will be broken."
Sara giggles at this, but the couple still pays no min to the team, which is why from Roy and Sara's angle they can see Felicity smiling when she turns her back to Oliver.

Roy points to Sara, blurting "Next week, thirty bucks, I'm moving it up."
Diggle looks for the return volley but Sara's thinking about it, so he jumps in first. "I'm down. I say first day on the job, this coming Monday."
Sara's giggles turn to a full blown smile from one dimple to another at her next words. "I'm in for both of those. I say two weeks on the job… and an extra ten if it's the elevator."
In return she gets a "Done" and an "In" from Digg and Roy.

When they all turn back, Oliver and Felicity are standing there watching them, Felicity almost looks surprised they're even there. Both are confused, till Felicity's eyebrows shoot skywards. Then all of a sudden she's rifling through her purse. She walks over and puts down a ten dollar bill on the table between the three teammates that surprised her. Catching on faster than they thought she would, she just says "on the elevator" and without another glance at any of them, walks over to her computer chair.

Cheers for getting to the bottom of my late night rambling/writing.
The mistakes are a result of sleep deprivation and that is entirely my fault. So the mistakes are mine too I suppose.