His Puritanism is so transparent. He’s asexual because he can’t get laid. He thinks people shouldn’t mix business and pleasure because he never gets invited to parties. He’s contemptuous of “drunks” because he’s never socialised with a drink or two.
He wasn’t invited to that party because in 2017, a pronoun badge was the full extent of his transition. He looked like a bad joke about trans women.
Plus I imagine he’s very boring IRL.
This is it, you hit the nail on the head.
Everything that he's never been invited to and been rejected from, he's made his identity part of his rejecting the thing. So it's become "you can't fire me I quit!" for every aspect of his life.
Nobody will sex him? He doesn't do sex.
Never been invited to a bar? He's too good for bars. Etc, etc.
And the worst thing about hearing him try to give adult advice, is that maturity wise, Jake is a child. He's never kissed anyone, he's never been on a date, he certainly never lost his virginity, he's never had a regular workplace job, he's never had any regular friends that he sees IRL.
But he's internalized the SJW "subjective reality becomes the world" technique, so he naturally thinks that he has a position to lecture people about his boring horrible lonely life, assuming that it somehow has relevance to anyone else, or that the milestones of adulthood that he never managed to cross, remain uncrossed for most people? Some people? Anyone at all?
He doesn't see how, despite his sarcastic and patronizing tone, all of his caveats and worries reveal him as a complete outsider.... He's never even been accepted into NERD culture, let alone society at large.
The strangest aspect for me, is that he doesn't see how alien his life experiences are to most people. I guess he thinks that the condemnation of all things masculine and social, which has been a side effect of the sjw encroachment into all culture, has basically given him an excuse to ride his antisocial hobby horses about every aspect of his life that's failed, and he's probably not wrong, that's the sad thing.