20 Awkward Questions to Ask a Guy

Man and woman talking

Show me a woman who hasn’t put her foot in her mouth at one time or another with a man, and I’ll show you a liar. Every single one of us – even the most sophisticated and elegant women in the world – has put their foot in the mouth from time to time. We have a thought and that thought makes its way out of our mouths about two seconds before our brain says, “Yeah, no…keep that one to yourself,” but then it’s too late. It’s awkward. So, so awkward. We mean well, we really do. But sometimes we don’t phrase things as well as we might have had we taken a few minutes to think that through.

With a girlfriend, we can laugh it off. With a guy, we have two choices: admit to speaking before thinking or play it off as a joke. Either way, prepare to see a recap of your most awkward moment on social media ASAP. On that note, we can’t stop you from making things awkward all the time, but we can help you by providing this list of questions you just shouldn’t ask a guy. Like, ever.

  1. Why do you do that?
  2. Can I meet your parents soon?
  3. Why did it take you 10 whole minutes to text me back?
  4. Why didn’t you answer any of my calls?
  5. Does your mom like me?
  6. How does it feel to be the less attractive brother?
  7. Wow, your brother is a doctor? Is he single?
  8. If me and your mom were both trapped on a desert island and you could only save one of us, which would it be?
  9. So, are you going to propose to me someday?
  10. Didn’t you just love my parents?
  11. Do you think my friend is prettier than me?
  12. Be honest, which one of my friends is hotter than me?
  13. If I wasn’t here, which one of my friends would you date?
  14. Is that it?
  15. What’s your annual income?
  16. What were you thinking the second you met me?
  17. What is it that I do that annoys you?
  18. Have you cheated on an ex?
  19. What were your exes like?
  20. Why don’t you join the gym?

Photo by Matthew Stockman/Getty Images


Leave a Reply