Jessica Pin Shares Dating Journey from 34 to 40 and Commitment Struggles
Last updated
8 hours ago
From ultimatums at 34 to weekly dates at 35, Pin kept high standards and ranked prospects, but since 36 she's demanded upfront marriage talks, even drafting a contract. Now at 40, a longtime friend's interest slipped away amid her pushiness, leaving her wary despite bar encounters and a preference for younger men. The thread sparked talk on dating timing, with some noting her shift from casual empowerment to frustration, while reports show many women over 40 now prioritize emotional bonds and independence.
Date: November 11th, 2026 8:27 AM Author: message board of ill repute
a preference for younger men tp
@jess_ann_pin
Jessica Pin
@jess_ann_pin
23h
No I wouldn't have. At 34, I had a hot, 6'4" 27 year old repeatedly giving me ultimatums to commit.
If anything I had too many options. I would have hundreds of matches. I would keep a rotating list of 10 ranked prospects.
At 35, after a breakup with a guy who admitted just lying the whole time, I was going on 5 dates a week and my standards were not high. I did actually go out with a 53 year old but the sex was terrible so I bounced. The guys who did finally want to date me seriously were the hottest ones and my age. I fell for one but then freaked out over a perceived dealbreaker because I was scared to get hurt again.
I never have lacked options. The problem is figuring out if men are real options or just wasting my time.
Since 36, I have been telling guys I do not want to date unless they are looking for marriage and kids. Every guy says he is down. I even had a whole contract at one point.
I am now 40 and my friend of 6 years told me he had been into me this whole time. I said I do not want to date except for marriage and kids.
He said our kids would be supermodels who look like me. He had remembered so many details about me over the years and had saved a bunch of candids he took that I didn't even know about from when we met.
I believed him. Honestly at this point I think he was genuine and that I screwed up by being pushy and then kind of an asshole, as people have explained.
There is still no lack of options, and if I go to a bar and walk around it's going to be the hottest guys who talk to me not the other way around. But I apparently have to assume most are just liars and fuckboys.
I also do not like older men. I do prefer younger and I reject double standards about this. Women have just as much right to choose what we like as men do and should be able to trust that men trying to date us are not just fuckboys lying. Honestly I think the young ones are less likely to be so. Any guy single and going for younger women at 55 is probably sexist and just going to keep trying to go for younger women. 🤮
Date: November 11th, 2026 8:32 AM Author: israelrimsmyasshole
There is still no lack of options, and if I go to a bar and walk around it's going to be the hottest guys who talk to me not the other way around. But I apparently have to assume most are just liars and fuckboys.
Date: November 11th, 2026 8:54 AM Author: Kenneth Play (emotional girth)
she's a megapoaster on twitter. i'm not saying you should read all of this post by her yesterday, but if you read any portion of it, you'll understand she's not well.
guy says
[your standards are too high, you wouldn't have dated a 55 yo man at 34 right?]
Jessica Pin
@jess_ann_pin
No I wouldn't have. At 34, I had a hot, 6'4" 27 year old repeatedly giving me ultimatums to commit.
If anything I had too many options. I would have hundreds of matches. I would keep a rotating list of 10 ranked prospects.
At 35, after a breakup with a guy who admitted just lying the whole time, I was going on 5 dates a week and my standards were not high. I did actually go out with a 53 year old but the sex was terrible so I bounced. The guys who did finally want to date me seriously were the hottest ones and my age. I fell for one but then freaked out over a perceived dealbreaker because I was scared to get hurt again.
I never have lacked options. The problem is figuring out if men are real options or just wasting my time.
Since 36, I have been telling guys I do not want to date unless they are looking for marriage and kids. Every guy says he is down. I even had a whole contract at one point.
I am now 40 and my friend of 6 years told me he had been into me this whole time. I said I do not want to date except for marriage and kids.
He said our kids would be supermodels who look like me. He had remembered so many details about me over the years and had saved a bunch of candids he took that I didn't even know about from when we met.
I believed him. Honestly at this point I think he was genuine and that I screwed up by being pushy and then kind of an asshole, as people have explained.
There is still no lack of options, and if I go to a bar and walk around it's going to be the hottest guys who talk to me not the other way around. But I apparently have to assume most are just liars and fuckboys.
I also do not like older men. I do prefer younger and I reject double standards about this. Women have just as much right to choose what we like as men do and should be able to trust that men trying to date us are not just fuckboys lying. Honestly I think the young ones are less likely to be so. Any guy single and going for younger women at 55 is probably sexist and just going to keep trying to go for younger women. 🤮
No that’s a smoking gun Ashkenazi name. Usually it appears as “Pine” but either way it’s the old semitic “name game,” typically originating as Pinsky or Pincus or similar.
My wife is the same age and has a similar physique but my wife's abs are a but more toned than this childless shrew despite 2 kids. Skinny jewesses can age well
Just looked up his gf and she is not my type but she will age better than my pale-skinned wife bc that chick is part moroccan jew. Olive skinned women go longer without getting all wrinkly
Date: November 11th, 2026 10:35 AM Author: AZNgirl with email addy CumTingWong@Handsome.com
for some reason i expected an AZNgirl but i see shes a dirty filthy kike looking slut, there's like millions of these bitches in NYC, SF, and big US shitties just getting railed by Chad and Vishnu left and right for years then they wonder wtf they still single at 40
Date: November 11th, 2026 11:17 AM Author: Oh, you travel? ()
is there even proof she's an IRL person. X.com engagement bait imo. idk why highly online men think pointing out female hypocrisy and deception is going to make a difference. it is utterly futile, nothing you "argue" with a woman registers at all.
Date: November 11th, 2026 11:30 AM Author: Darnell
she had her labia cut off at 18
But after a cosmetic surgery when Ms Pin was a teenager that she says left her with scarring and reduced her clitoral and labial sensitivity, the daughter of a plastic surgeon has dedicated herself to educating the public and the medical community about the female equivalent to the penis
Date: November 11th, 2026 2:29 PM Author: ,..,,,,,,....,,,...,
Jesus Christ, she is a real person and recent crashing out is at best the #2 craziest item in her bio. Elective underage labioplasty with no actual medical reason had not even occurred to me as a crazy thing a crazy woman would do. Why can’t she be a demoralization psyop? Can we send these people to blue sky so Twitter can be usable again?
"She believes surgeons underplay the risks of the surgery while making claims for which there is little evidence
After her own procedure, she believes the dorsal nerves of her clitoris were severed, permanently erasing sensation.
“Surgeons claim protruding labia are ‘hypertrophic’, which means overdeveloped,” she says, “but it is unreasonable to claim half the population [of women] has an excess of any anatomy, yet this is what they do.” (According to a 2017 Danish study, 56 per cent of women had visible labia minora.)
Date: November 11th, 2026 2:21 PM Author: Pumonymous
This thread doesn’t even scratch the surface. If you scroll a few days back into her tweet conversations or search her name, you’ll see that the recent tweets are part of a multi-day crash-out over a Chad rejecting her.
She even posted his phone number and asked everyone to text him and ask why he was giving mixed signals or whatever (the phone number tweet has been deleted but if you dig you can see all the replies being like “wtf is wrong with you”).
Take a look at this video she posted showing her sending him multiple long insane texts with no reply, until he finally got back to her a couple days later and promptly ended it with her: