Questions To Avoid On A First Date

Over at, writer Scott Alden has a piece up about how to keep date conversation interesting. He cites a recent study conducted by psychologist Dan Ariely, which found that when communicating on dating websites, most people are boring as fuck because they’re afraid to ask provocative questions.

This stands to reason, since most folks tend towards the safe and conventional in their public lives.

But to remedy the problem, Ariely made a curious suggestion — he recommended asking questions that aren’t just provocative, but are downright offensive, such as: how many people have you slept with?

In response, Alden accurately points out that one needn’t be a douche in order to be interesting. We here at The Gloss salute that notion, and so, in our never-ending quest to rid the world of ‘bags, here are some questions you shouldn’t ask on a first date:


Our dating page, brought to you in partnership with HowAboutWe is far from boring. Head on over, suggest an outrageous date, and find someone who will join you!

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    • booch

      oh my god why do they always ask you to smile??? stop it stop it.

    • Magda

      Hahaha… That actually just happened to me! The smile one I mean… But it got me two free drinks from some guy at the bar, so it wasnt all bad. he said, and I quote, “I brought this for you because I want to see that smile all night”… which was cute even though it kind of implies that he was trying to get me drunk… so, kind of creepy, but cute. Right?

    • Nikita

      The next time a man tells me to smile, I will kick someone in the dick!

    • Amanda

      Someone told me that the best answer to random people telling you to smile is, “I’m sorry, did you say something funny?” which I feel hits the nail right on the head.

    • Stephanie

      Finally someone pointed out how ridiculous it is to ask if a tattoo hurt! I have one, a very small one, and first question is always… “did it hurt?” No Duh! (btw thanks BlissTree for bringing that awesome phrase back!)

    • lisa

      haha yeah about the tattoo question. of course it fucking hurt! also never ever grab or touch anyones tattoos with out asking them. this has nothing to do with first dates other than when i was out with my boyfriend on our first date one of douches at the table next to us grabbed my arm and asked me about my tattoo. normally i am a super bitch but i was trying to make a good impression. now he knows after 2.5 years that i don’t tolerate such behavior as well as i did that night :)

    • Diana

      I can’t say I agree with the sex positions one and the ‘Smile!’, of course in a proper context. It would be quite complicated to explain the exact context, but it exists.