Because Jim really thinks he’s a cool young hip dude, or that he can appeal to young, hip people. Everything he says or does is some horrible attempt at marketing.

I guarantee you somewhere buried in his awful broken retard brain was the thought, ”If I start talking about fucking trannies, chick will like me because I’m so progressive!”

"Girls say they want honesty, and I give em honesty and they don't know how to take it!"

It's almost as if there's a good reason most people hide their disgusting fetishes

Because the 22 Norwegian trans cam model rejected him, now he's trying to move on.

I think it’s a case of arrested development mixed with delusions about his level of success and prosperity.

he thinks it’s cool to cheat on your spouse constantly

who would ever want the risk of this bug chaser bringing home a fresh case of AIDS

that’s easily one of his lowest traits

Has jimmy bragged about cheating or something?

I can’t remember him doing that but he’s completely bankrupt morally so it wouldn’t surprise me.

He has. He’s often said that as soon as he’s in a relationship he starts sneaking around (except for his most recent relationship with that European guy).

I always took this to be a lie that he thought made him sound more attractive to fans, and raised his value to his partner because he could so easily be with someone else. But the reality is he had like 4 girlfriends in his entire life of desperately trying to have girlfriends.

I think it’s because he sees other people around his same age pulling attraction young woman & thinks he deserves that too. It’s not so much about Jims age that’s the problem but the problem is really just Jimmy himself. I know many non-famous older guys who date or even marry good looking girls 15 or 20 years younger then themselves & many of these females are actually intelligent & grounded individuals. But the problem is Jim isn’t one of these guys I’m talking about, Jim’s an awkward guy who has no natural charisma when it comes to getting ladies. Older men in healthy relationships with younger women are usually are handsome life long ladies men who are sercure in themselves, slightly overconfident & successful not only in their career but in all other facets of life. These are all characteristics that the worm doesn’t possess, he thinks just because he has a little fame & a little wealth that automatically he’s supposed to have a piece of ass 20 something year old girl to adore him but that’s not how it works unless he gets some trashy chick who’s looking for a payday.

entitlement

Jim wants actual love from a 25-year-old.

The gap between a 50-year-old man and a hot, 25-year-old woman can ONLY be bridged with two things: (1) An extremely good looking guy; and (2) Lots and lots of money in that guy's bank account.

Plenty of women will do the sugar daddy thing with an average/ugly guy, but she'll only be there for the money and she'll cheat on him.

IOW, to get what Jim wants, he needs to be extremely attractive and extremely rich. He's not either of those things. So he'll never get what he's looking for.

Intense delusions

To give himself a reason why he's alone. Like all incels, his "standards are too high."

He's a dickhead.

Girl?

After finally at long last putting 30 years of sissy cum-slut fantasies behind him (so to speak), Jimmy wants to pick up where he left off before his demented fetishes overtook his entire life.

Jim has money, some fame, and (despite what this sub is pushing) isn't the ugliest person on the planet.

The biggest barrier for Jim is that he has endless hours of radio and book pages dedicated to his sexual deviancy, including tranny fucking. That would be fine with some dumb liberal 20-somethings in New York, but he also has hours of racial material out there.

He's too disgusting for normal girls and too racist for the young generation of hippie girls. Even if he reeled in a 25 y/o, it'd be hard to keep her.