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Single NYC woman swears off dating after having the ‘worst first date’ with an older ‘egomaniac’

News RoomBy News RoomAugust 24, 2025No Comments4 Mins Read
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Single NYC woman swears off dating after having the ‘worst first date’ with an older ‘egomaniac’
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Oh no, that’s bad.

Dating in today’s digital age is no easy feat. And while it’s normal to have the occasional bad first date, one Gen Z woman’s recent experience with an “egomaniac” almost twice her age took the cake.

As many young daters do, 25-year-old Caitlin took to TikTok to debrief after a wild — not in a good way — first date, and collectively people’s jaws were on the floor after hearing her describe what happened.

In a video with over 400,000 views captioned, “Storytime about my date with a 43-year-old egomaniac,” the Gen Zer shared her experience: “About a month ago I went on the worst date I’ve ever been on in New York City and I need to talk about it.”

She met the guy while out at a “random bar” in the West Village. “He was definitely older, which I’m not usually into but he seemed really cool and nice and well dressed and all the things. So when he asked me out, I said yeah.”

The next week, she met this older stranger at a bar in the West Village and upon arriving, she noticed that “he’s sitting at a table with six of his guy friends,” which obviously is bizarre for a date of any kind but especially a first date.

“Then two interns for his company also join us. I just feel really uncomfortable right off the bat,” Caitlin explained in her viral video.

Her date must have sensed she was feeling this way so he requested a seperate table for the two of them.

Yes, things got progressively worse from there.

The Gen Zer’s date asked how old she was and acted relieved when she said she was 25 because “21 and 22-year-olds can’t keep up with him intelluctually but he feels too bad for 30-year-olds because they’re so desperate.”

The guy continued to talk about himself, show off pictures of him with celebrities which caused the woman to think to herself, “This is so embarrassing for a 43-year-old…”

The dinner ended and after she declined the goon’s invite for a drink next door, he told her he wouldn’t order her an Uber home unless she continued the night with him.

She can clearly get herself a ride home but she ignored her gut and still went out with him. The same weird shenanigans continued, in which she finally called it a night and while waiting for her ride home, she heard his friend in the background ask her date if he got “rid of that girl yet?”

Well, the commenters really went off on this guy.

“He just wanted to impress THE MEN… Because a man is what they really want.”

“You’re too gorgeous to not have stronger boundaries.”

“He was straight up just showing you off for free that’s wild.”

And sadly this is just one of many bad dates women have been on lately in today’s bizarre dating world.

Another woman went on a first date with a guy who didn’t offer to pay for her coffee — so she quickly put a stop to any potential dates he might ask her on.

Khristina is an Australian influencer who shared a screenshot of a text exchange between the cheap guy she went on a coffee date with in a TikTok video that read:

“So you’re canceling the date because I didn’t pay for your coffee on the first date?” the man asked.

Yes,” she replied.

“Well you definitely have an attitude problem,” he responded.

“I don’t have an attitude problem. You have a problem with my attitude, which is not my problem,” she argued.

She mentioned how people can do what they want — which means she doesn’t have to go on a date with a guy who can’t even pay for a $5 coffee.



Read the full article here

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