Is it weird to ask someone "what's the worst thing you've ever done" on a date?

I love to ask this question to all my friends. I just love hearing about these types of things. Would you be weirded out by this question?


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Most Helpful Girl

  • How about rephrasing it to "craziest thing ever done" instead? That way it limits the pool down to things one can laugh over instead of potential downers.

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Most Helpful Guy

  • Yes it is weird and likely offputting, because most people are ashamed of that. So making them feel guilty, sad and regretful when you just met... not good for a date lol

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What Girls Said 7

  • One guy asked me that but I had nothing to answer because I've never really done anything bad.
    But then he went into a story about how he got arrested and it was a total turn off to me.
    So be prepared for her to lose interest or you to lose interest based off that answer haha

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  • It's not polite conversation for a date but is fine for friends in the right situations.

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  • What would you do if your date told you that the worse thing they ever did on a date was kill their date for leaving? Lol

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  • Kinda

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  • Nope lol

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  • I'd answer but with something cute or funny, nothing serious or sexual.

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  • You're on the right track asking questions to get your date to open up and then to share an experience in return.

    Maybe take it down a notch in intensity, though. And stay positive - nobody wants to hit on downer issues on dates. Save that for when you're close to each other.

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What Guys Said 2

  • It's different and not good date conversation.

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  • What if they said they killed 20 people by driving over them? they were in a situation where they were in an alley way and guys with baseball bats, if they didn't run them over then the person in the car might bet beat up?

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    • Honestly, I laughed at that. I wound want to know that sooner rather than later.

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