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She Went On A Date With A Guy Who Asked If She Was Worried About Being Single At Her Age And Explained Why He Split Up With His Ex

profile Emily Chan | Dec 27, 2025
Dec 27, 2025
Young professional woman using smartphone during dinner
Lomb - stock.adobe.com - illustrative purposes only, not the actual person

When TikToker @holdmeliable went on a first date with a slightly younger guy, the casual meetup turned into a wildly uncomfortable interrogation, complete with backhanded compliments and unsolicited judgments.

He only asked her one normal question throughout the entire date, which was where she liked to go out in the city. She told him she loved the West Village, but he said it didn’t really seem like her vibe because it’s associated with expensive dinners and cocktail bars.

This rubbed her the wrong way because they had just met.

During the date, he also told her about his last girlfriend and why it didn’t work out between them. Then, he mentioned that a lot of his 28 and 29-year-old friends were worried about being single at their age and asked how she was feeling about it because she was 29.

She explained that her mom was 34 when she got married, and there was a bit of divorce on both sides of her family, so she wasn’t too concerned about still being single.

“And I was kind of going through the record, and he’s like, that’s too much for me to know; I don’t need to know that,” she recalled.

“You asked if I was worried about being single, so I’m explaining how I’m not.”

“Anyway, the whole night was just question after question and then him saying out loud, being like you’re really cool. Your personality is interesting, you speak your mind, and you’re not like other girls. It was horrible.”

At the end of the date, he walked her home, and when they got to her door, he started talking about how things felt off and was thinking that he might not see her again.

Young professional woman using smartphone during dinner at upscale restaurant, smiling while checking social media
Lomb – stock.adobe.com – illustrative purposes only, not the actual person

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She told him she needed to go because she had something in her eye. Later, he texted her, asking to see her again, and she had to gently let him down.

The comments section was filled with similar dating horror stories. First dates are not interviews, so if someone makes you feel like you’re being graded, it’s probably okay to fail the test on purpose.

“This guy’s opening message on Tinder to me was: ‘Since you’re above the age of 30, I assume you’re looking for a husband.’ Okay, Mrs. Bennett,” commented one user.

“Girl, I was asked the same thing once, and I was like ????? I’m worried being here with you, lol,” stated another.

“I went on a date that also rapid-fired questions at me the entire time (have you ever been to Vegas? Would you want to go? Do you play mini golf? Do you like living in CT? Nonstop. And he had a super awkward laugh after every single thing he said, to which our waitress commented, ‘Wow! That’s quite the laugh,'” added someone else.

@holdmeliable

Please comment your horror stories so I feel better?? #date #dating #nyc #storytime

? original sound – holdmeliable

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By Emily Chan

Emily Chan is a writer who covers lifestyle and news content. She graduated from Michigan State University with a degree in... More about Emily Chan