19 Most Cringeworthy Questions Men Have Asked Women on Dates

When it comes to first dates, some questions make a good impression, and others really kill the mood. Someone recently asked, “Women, what is the most stupid question you’ve been asked on the first date?” Here’s how the internet responded.

Are you really attached to your children?

Are You Attached To Your Children
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I had a guy ask me if I was really attached to my children. When I didn’t answer and just made a questioning face, he went on to explain that he doesn’t date women with kids (single mom was clearly stated on my profile), so he was hoping I’d say no and… just get rid of them, I guess?!”

“People that have a preference but then go out of their way to find someone that doesn’t fit said preference in the hopes that they’ll change will never fail to amaze me.”

Are you into women?

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I had a girl ask me if I was into women… while I was on a date with her, a woman.”

“I’m a woman who dates women, and sometimes there does seem to be confusion about whether we’re on a date (even if we met on a dating app).”

How heavy is your flow?

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Once a guy didn’t ask me a single question for two hours, so I decided to point that out. He got annoyed, sighed, then said, ‘How heavy is your flow?’”

“Maybe he meant your rapping ability…”

How long have you been Asian?

How Long Have You Been Asian For
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“Um…my whole life?”

Since Tuesday. I was Egyptian last week.”

Will you marry me so I can get a visa to stay?

Will You Marry Me So I Can Get A Visa
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Oof, I had one of those too. I will say that I appreciated the honesty and not wasting my time.”

“At least he cut to the chase. Did he at least pick up the tab before proposing?”

My place or yours?

My Place Or Yours_ After A Boring Date
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I’d say the worst first dates were the ones where the guy asked me virtually no questions during the date, but when we were getting ready to leave, asked either, ‘When can I see you again?’ or worse, ‘My place or yours?’”

“Both. You go to your place, and I’ll go to mine.”

Have you ever killed someone?

Have You Ever Killed Anyone
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I was in the military, but that is not a good question to ask someone.”

“That’s a question I’d expect from an eight-year-old boy, not a grown man.”

Are you going to continue being nice to everyone all evening?

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I was polite to our waitress, and he asked if I was going to continue being nice to everyone all evening?”

There is no bigger turn-off than a person who treats wait staff poorly.”

Why can’t you wear more natural colors?

Always Having Women Think You’re Hitting On Them
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I honestly can’t remember if it was date one or two, but I was wearing orange eye shadow that looked splendid on me, and the guy asked why I couldn’t wear more natural colors. I was like, define natural. And he couldn’t really explain it to me after I drilled him about it.”

“He was probably trying to say ‘neutral’ but didn’t know the word.”

What if I brought you all the way out here to murder you?

What If I Want To Murder You
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“I went on a first date, and we went on a hike. Towards the top, he asked, ‘What if I would’ve brought you all the way out here to murder you?’ I told him that I watch and listen to too much true crime to come unprepared for a first date and that four of my friends have my location and his first and last name.”

“I walked home with a guy after a church program for young adults (I was about 19-20 at the time). It was my first time meeting him, but he seemed harmless enough as I literally met him at church, and he seemed quiet and polite. We were almost to my house, walking down a darker part of the street, and he said, ‘You know, I could assault you right now.’ He laughed like it was supposed to be funny, but It was the most scared I’ve ever felt in my life.”

Can I borrow a strand of your hair so I can floss my teeth?

Can I Borrow A Strand Of Your Hair
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It was weird, but we’re married now!”

Borrow even. So he was going to pluck one of your hairs out, floss his teeth with it… and then hand it back to you?”

What’s your body count?

I Have To Keep My Body Tight For My Husband
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I had a combination of this coupled with ‘how many White men?’ That date lasted 16 actual minutes.

“Seriously, people need to get trained on what to say on the first date.”

Can you rehome your cats for me?

Can You Rehome Your Cats
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‘Can you rehome your cats for me? I don’t like cats.’”

“Was it on your first date? Unimaginable.”

Do you want to get a matching tattoo?

If You Keep Getting Tattoos, You_ll Never Find A Husband
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Had a guy ask once if I wanted to get matching tattoos. On the first date.”

“Same, and he was already looking for designs during the date.”

Are those all-natural?

Why Can’t You Wear Natural Make-Up
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I would’ve said, ‘No, they’re all supernatural.’”

“Very haunted. They’re so big because they’re full of spirits.”

Why are you still single?

How Are You Still Single
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Someone asked me that question once, and I just told them I was crazy. Made up a whole list of symptoms that are clear red flags and let them figure it out from there.”

“People actually ask this? It’s not a job interview!”

How much money do you and your parents make?

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Gold digger vibes.”

“I had a guy tell me that he knew my parents weren’t rich by how they acted. And this was a bad thing. I was so confused about why he cared!”

Are you a lesbian?

Denying Lesbians
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His ‘logic’ was that I don’t wear makeup and I play sports?”

“One time, I had a woman I went out with saying, ‘Oh, I can totally see that you’re bisexual now. Makeup, and boy’s clothes as if being bisexual is splitting being femme and boyish right down the middle.”

Do you want to buy my dirt bike?

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So, obviously not an awesome date, but I assume the dirt bike was fun, at least?”

I mean …if he makes you a good deal?”

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