Why is Barry currently in a maid dress? It's a long story- okay, not a long story, but it's an embarrassing one.
He and his friends were doing a game night, something they got together for every once in awhile. They were all laughing and joking, not taking anything seriously and just having an overall good time over a few drinks. Then, one of his friends suggested that they start introducing some stakes to the games. Didn't seem like a big deal, just an embarrassing text here, or a weird drink combination there, just enough for people to actually start getting competitive.
And then the maid outfit was brought out, and it was declared that whoever lost the next game would be forced to wear it for the rest of the night. There were laughs and snickers murmuring throughout the room, but people really geared in; Nobody wanted to be subjected to that humiliation.
The game of choice had been Mario Kart, something Barry happened to be rather good at. He was coasting along in first place, winning the first race of the circuit no problem. But midway through the second, he glances over at the one currently in last place. He can see the panic, how clear it is that they don't want to wear that stupid maid dress.
With a grimace, Barry allows himself to get hit by a blue shell, then another, then slip on four consecutive banana peels until he's in last place for all of the remaining races.
And now, he's standing in the middle of the living room, wearing a maid outfit that's just slightly too small for his muscles, slightly too short for his height, in thigh highs and little black shoes while wishing he could crawl into a hole and die.