If it was a 20 year old real woman it's one thing. But this is a sexually confused boy.

Is it actually confirmed that its a transsexual?

According to people who heard the show. I can't listen to that shit so I can't confirm for sure. But they seemed serious.

If he just wanted a 20 year old hot chick, there's a million of them in New York he could try to pick up. But trannies are rarer, so it makes more sense.

He's 49 years old. He's hardly a "boy".

No, he said that he wouldn't show her pussy and didn't confirm what it looked like or even if it existed.

Or wanted to show her the miracles of modern surgery.

What? you don't think 20 years old are hot? especially with a nice solid cock? Get you're head out of you're ass.

Honestly, the whole "is it gay to like a trans girl?" question is stupid. If you like a chick to have a dick, go for a chick with a dick. If you don't, stick with pussy.

Any time someone sets aside their own personal wants because they're wondering "well, what if this makes me gay?" or whatever I just assume they were called pissy-eyes as a kid and had to watch spaghetti fall down the wall.

Have sex with people you wanna have sex with and don't give a shit. Fuck it.

Depends on how big their dick is.

Understandable. Some like 'em big and dominating, some like 'em small and adorable. Everyone is entitled to their own taste.

So to speak.

Have sex with the people you wanna have sex with and don't give a shit.

Agreed. Even if the people in question don't want you to and go crying to the police like a bunch of babies.

Especially if they don't want it. You need to be active in changing people's lives.

He's going through what men usually go through in their teens

Experimenting with with boys?

He got sober at 18 and has let a book, his higher power, and meetings full of degenerates guide him through life instead of having experiences and maturing like a normal person

Exactly, this is a man that lived with his parents until he was in his 30s. Jim has the emotional maturity of an entitled 18 year old. You can hear it whenever he fucking sniffles before saying something "deep".

In love with a bitch who just entered her 20’s? This I’ll end well

There's nothing wrong with the age gap. But Jim believing he's in love with her is kinda sad.

It's embarrassing how these old bastards keep getting played by young girls. All their money won't change the fact that they will always be losers.

You're a faggot. 20 year Olds are fine. The problem is there is no way this thing is in love with Jim. Young people are fickle.

It'll be a fun 21st birthday for her. When the clock strikes midnight she does 1 shot & Jimmy drives her to rehab

She's european so she's been drinking for years. Jimmy will have to convince her that something deeply ingrained in her culture is a "problem".

The worst part of this is listening to him tell every guest, "I don't name call with this one." 49 years old and finally realizing this?

And every person he says this to must just blankly look at him thinking, "What are you, 15 years old?" My God.

Heels!

Of course Chatty Cathy finds himself into all of the little gossip threads, fucking woman.

You're in the same threads.

Bisexuality has driven this man to insanity.

Buysexuality has. Tss

I'm 31, for and relatively attractive and I would never put up with a modern 20 year old outside a simple one night stand.

Are you his fucking aunt!? You people are CUNTS

No 20 year old wants a 50 year old, especially one who looks like Jim.

I guess the years of eating 5 almonds and a bean sprout with mustard a day stunted his emotional development. Also, sam looks like a cro magnon car salesman

It's a pretty sad story to follow. This weirdo is probably bankrupting him as we speak, bleeding him dry while he embarrasses himself pining away for "her" in public. How's he ever going to come back from this after "she" finishes him off?

maybe she is a fan, he has people that think he is funny, i think his standup is great, i could see a young girl falling for him, she is probably as fuct up as him, but i dont think he is being used, and who cares if he is unknowingly just renting the pussy short term, im sure he is getting all he wants from the relationship at this time.... there is someone out there for everyone, i dunno why you guys have to be shitdicks about a messed up little man finally being happy for a change, look at gilbert, he met a woman that is legit in love with him, sure she wasnt 20 when they met, but she isnt using him, she just weirdly enjoys everything about him from his crazy voice to his 40 yr old joke routine.

also jimmy has had actual relationships with moderately normal women before, even women arguably more successful than him like the chick from brooklyn 9/9 that he was banging for awhile....and most his tranny shit could be a madeup character, it's believeable that he has done some gay shit, but his uncle paul shit could lead one to think he may actually be a pedo too... it helps in radio to fake flaws and seem relatable, his flaws are insanely fucked up, but doesnt mean its all real, his addiction stories are all bullshit, he clearly didnt have an actual drinking problem, guy stopped when he thought it may be an issue, he just likes to pretend he has experienced things when he talks to people who actually have, and over the years of talking to real mongoloids on air, he has upped his bullshit to strangely try to compete for the title of most fucked up, and its hard to know what is real anymore....like with stern, that jew lied for over 20 yrs about everything, he is still a fake pos, even his interviews are fake as shit now as he rips off the style of barbara walters and has is people wrrite up shitty puff questions, and try to find lame ways to get guests to cry...instead of asking interesting questions to manson, or maybe talking about what it was like fucking that loony bitch from westworld, he spent 20 mins trying to get him to cry about his dead dad....anyway, im off topic... my point was we dont really know what the real jimmy is like, radio jimmy is a scum bag, but real jimmy could sit at home reading the bible for all we know, and either way, its not that crazy that someone could actually love him.