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"It’s a costume party, Oliver. You can’t not wear a costume. And honestly if you’re going to keep up your Manchild Billionaire Act then this is the way to do it." Dig said, he was grinning and holding up a tangle of fishing nets and a trident. Oliver had been invited to the Wayne Foundation Charity Ball, as a burying of the hatchet with Bruce Wayne, an old school mate. They hadn’t liked each other much when they were younger and this was going Bruce’s olive branch.
Wayne Industries was going to be partnering with Queen Consolidated on a huge technical project and it wouldn’t do for the face of Queen Consolidated to not show up to the party. Oliver would be taking Dig along in his official capacity as a bodyguard, and Felicity in an unofficial capacity as a second set of ears. Gotham’s own vigilante had been protecting the greater good for about 2 years before Oliver had come home, and he wasn’t going to miss the opportunity to do some looking around.
“Dig, I can’t wear this! It’s see through. I know Manchild Playboy is a cover but the last time I was arrested for indecent exposure I had just graduated high school.” Oliver looked at the mess, it had been Felicity’s idea. He was going to be Poseidon and was resigned to being uncomfortable and freezing for the remainder of his night. Felicity was going as Barbarella, on Dig’s recommendation, and she was perfectly comfortable, even without pants. Dig was going to be Han Solo, also Felicity’s choice. She had said that if Diggle had to go and be the bodyguard Oliver had no use for then he might as well have women throw themselves at him.
"Only high school? Wow. I know we’re using the jet, but I do want to get to the hotel early. People talk over food and if you want to know about the lunatic who dresses like a bat then I’m going to have to start eating and mingling early while you talk shop." Felicity said, looking up from her rig. Barry had sent over a whole slew of articles on the figure Gotham PD had taken to calling the Batman. The plan was to have Oliver only make a minor embarrassment of himself, and have Felicity pretend to get uproariously drunk so the three of them could leave early and The Hood could do some exploring of his own.
Oliver was hoping that Bruce wouldn’t make him stay too long, Bruce hated throwing parties like Oliver did, but as their parents children, it was their birthright and the Wayne Foundation was as legitimate a charity as any other. He remembered his parents seeing on the news that Thomas and Martha Wayne had been murdered, he’d only been a kid at the time but Robert and Moira were in the same social circles as the Waynes and Moira had been to the same prep school as Martha when they were girls. Meeting Bruce at school had been an event, both boys were headstrong, fierce, and entitled in the way that only the disgustingly privileged could manage. They got into scuffles over grades, girls, and sports until Oliver decided that getting expelled was far more fun than actually attending classes.
Bruce had spent the better part of his late adolescence and early adulthood travelling, insisting that it had been his mothers dearest wish that he’d see the world. Oliver had rolled his eyes when he saw the headline, it was a publicity stunt. He had probably just gone to rehab or taken an extended holiday in the Mediterranean. They had only spoken over the phone a few times, as the better part of the deal was negotiated by the lawyers and the boards, not the company figureheads as Bruce had so politely put it. He’d be going as Zorro, and he was thrilled to be seeing Oliver after all this time and was even more thrilled to meet Oliver’s date.
"Mingle away, and make sure you avoid any of the older women. Gotham socialites are a whole different breed of nasty. I don’t know how many times this guy has done the rounds for the wealthy but maybe one or two have had an encounter they’ll tell you about if you get them to drink enough."
A text from Oliver’s pilot rousted the three of them from out of the lair, and they headed out to the airport. They were packed for three days, and Felicity made sure she had enough tech to spot for Oliver when he changed and did a bit of looking around. If this Batman truly worked by himself, he probably didn’t have anyone to hack cameras for him so they had the edge. They settled in and the jet took off, any other thoughts occupying their heads gone, with only an interesting nigh ahead
"Felicity, I know I said to avoid the older women, avoid Bruce too. He can be a bit-" Oliver started to say before she cut him off, Diggle watching the exchange with a smirk. "Handsome, charming, generous, kinda flaky, doesn’t really do any work at his Fortune 500 company, and a total ladies man? Now who does that sound like? Makes you wonder what he’s hiding."
Oliver almost choked on his water, and Felicty turned to high five Dig who had burst out laughing. “The only thing Bruce Wayne has to hide is his scorecard! I’ve stolen 3 of his girlfriends, and that was before we turned 18.” Oliver’s cheeks flushed and his eyes held a frosty glare in them that only showed when he was feeling competitive.
"We’ll see, won’t we. Felicity won’t be the only one with an ear to the ground tonight. Does Wayne have a bodyguard that might be willing to commiserate?" Dig asked, stretching out and adjusting the pillow he’d brought with him behind his head.
"Nope, just the butler who raised him, Alvin or something. I can’t remember. Older guy, English. "
"Butlers will do just fine. Let’s keep whatever spectacle you make of yourself off of the first page of the Gazette though. You said the One Percent were nasty, they don’t have a patch on the criminals. All the freaks end up in Gotham and I’d rather them not try to take a shot at you in broad daylight."
Oliver nodded, and the three of them all attempted to nap, read, or hack into the GCPD computer system. Felicity was making her own fun since in a few hours she was going to have to play dress up with some of the richest women on the east coast. Even Oliver’s costume wasn’t enough to keep that thought out of her head. She’d really prefer to stay in the hotel room and work but Oliver Queen, billionaire manchild needed a companion and the lovely blonde assistant was the socially acceptable non-date he needed. Maybe Gotham’s vigilante was looking for a girlfriend, she had a type now.