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30 Playful Questions To Ask Your Crush To Keep The Convo Going

If you've never felt tongue-tied while talking to a crush, then you're either lying or you're much cooler than the average person. When you hit a lull in conversation, it's natural to panic, but asking your crush a thought-provoking question can help keep the ball rolling. And while you can always keep things casual with a question about your crush's interests, hobbies, and aspirations, it never hurts to add some LOL-worthy Qs to the convo. There are plenty of playful questions to ask your crush on a date or over text, and the answers will likely reveal more about that person than you'd expect.

Sometimes it's fun to ask questions that delve into your crush's past and reveal deets about their history. You can also try questions that test their personal opinions (though it's probs best to stick to non-contentious issues). And of course, it's always illuminating to ask about someone's pop culture preferences. Whether you're looking for questions that get a little flirty or questions that spark interesting discussions, these random AF inquiries are sure to inspire hours of convo. The best part: These questions all work just as well in person, over text, on dating apps, or through DMs.

Personal Questions

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  • What's your grossest hidden talent?
  • What's your most embarrassing childhood memory?
  • What's the worst haircut you've ever gotten?
  • What's the strangest nickname you've ever been given and how did you earn it?
  • What's the most awkward thing that's ever happened to you on a date?
  • What's the worst thing your parents have ever caught you doing?
  • What was your first-ever email address or screen name?
  • What part of a kids' movie scarred you for life?
  • What's a fashion trend you used to rock but now totally regret?
  • What's the weirdest thing you've ever done at someone else's house?

Opinion Questions

  • What's one thing that never fails to make you cringe?
  • What do you think is the best way to prepare for a zombie apocalypse?
  • What is the worst name you can think of to give your future child?
  • What do you consider the worst condiment?
  • What chain restaurant would you refuse to eat at even if you were desperate?
  • What body part could you live without?
  • What do you think is the most embarrassing thing to buy at a convenience store?
  • What do you consider the worst smell in the world?
  • What social convention do you find the most annoying?
  • Which mythical creature do you wish was actually real?

Pop Culture Questions

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  • How long do you think you would last in the Hunger Games?
  • Which Hogwarts house would the Sorting Hat most likely put you in?
  • If you could pick any celebrity to officiate your future wedding, who would it be?
  • If you could date any fictional character, who would it be?
  • What actor would you pick to play you in a biopic?
  • If your life had a theme song, what would it be?
  • Which Marvel superhero would you be if you could choose?
  • What movie would you love to see turned into a musical?
  • What fictional friend group would you like to join?
  • What celebrity do you wish had their own reality show?

With these fun questions, you can say goodbye to awkward silences with your crush forever.