The only parties Bob ever went to as a young adult (or likely even as a teen) were either family affairs or when his slightly more socially functional brother let him tag along to something Chris was attending with his Blockbuster Video coworkers.
As a reminder, this is what Bob looked like as a late teen:
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He looked like a younger, fatter Kengle, had at least four tits, dressed like a slob, and you can practically smell him through the screen. Bob likes to trot out these stories about the MIT/Harvard/Boston College parties that he was definitely attending on the regular every now and then. I recall that, during the Kavanaugh confirmation hearings when that one liar/loon showed up claiming that Kavanaugh was participating in gang rapes at parties, Bob was posting about how obviously true her story was, and he knew it because he went to lots of parties and saw things like that firsthand from his dreaded mortal enemies: the frat boys and college athletes.
He wasn't dating a lesbian stockbroker or crashing college parties or beating Harvard students at beer pong. I'd bet Bob was doing the same thing as a college student that he does now: spending the overwhelming majority of his time alone, in a dark room, staring at an electronic screen passively consooming mass media and way too many unhealthy foods/empty junk calories. The biggest differences are that he drinks a lot more now, and he can shit out his shallow thoughts on twitter. Twitter isn't real human interaction, of course, but it's the closest thing to it that Bob ever gets.