It wasn't so much that he wanted to get his ass kicked, but rather that he didn't care anymore if he gets his ass kicked. I think Brandon was in need of a real human connection with another person, and he was being tired of the superficiality of the big city. He doesn't know how to get a connection with another human in NYC, because all the people he meets are superficial, selfish and are only after being associated with success (his success; and often through sex). Everyone he meets is after casual sex, and dismissing any attempt at a meaningful relationship. (Brandon thought his female work colleague was different and that he could have a meaningful relationship with her, but eventually he found out she really wasn't; that's why he couldn't continue to have sex with her. He realized that in her eyes, he was just a "score" (or that his behaviour was corrupting her into that kind of mindset), and he didn't like that.)
The girl at the bar was a skank. She was eyeing Brandon because she regards him as an upgrade (her own boyfriend was a blue-collar guy). Brandon knew her motives and that she shouldn't be making contact with him. So he takes it to the extreme by grabbing her crotch and fondling her in such an overt manner in order to make a point: that she's a skank. He's essentially trying to insult her and scare her away, because he actually doesn't appreciate her attention. But instead of being insulted, she lets him do it. So he makes it a point to the boyfriend, showing him what a superficial skank his girlfriend is (and how rotten relationships in this city are).
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