Play the 21 Questions Game with Your Crush, Thank Us Later

Nothing is more exciting than liking someone new. A whole world of possibilities—from first kisses to moving in together—opens up before your eyes and you’re basically the star of your own romantic comedy. The only downside? Since you likely don’t have the Bridgerton writing staff whispering in your ear, it’s easy to get tongue-tied around your crush. But lucky you, we’ve got a trick that makes the ~getting-to-know-you stage~ less anxiety-inducing and more fun. Enter: the 21 questions game.

Asking the right questions (and actively listening to the other person's answers!) is kinda like a dating superpower. “It shows genuine interest and encourages your crush to share their feelings, beliefs, and experiences,” explains Anastasiya Pochotna, a relationship and dating expert at Flirtini. “Physical attraction is one thing, but true compatibility reveals itself as you delve into each other's personalities, backgrounds, and shared interests.”

The 21 questions game turns getting to know each other into something far from an interrogation. “Even the silliest questions can reveal deep insights into someone’s personality,” says Shan Boodram, Bumble’s sex and relationships expert. “This game keeps you from monopolizing the conversation and demonstrates genuine interest in the other person. Plus, it’s fun!” In fact, discovering shared obsessions over TV shows or music might lay the groundwork for a strong relationship.

Whether you’re on a first date, flirting over text, connecting on a dating app, or navigating a new situationship, bookmark this page to spark conversations about more than just the weather.

How to Play the 21 Questions Game

The good news is this game is suuuuper easy, so you don’t have to memorize a bunch of rules or anything. Very simply, you take turns asking each other the questions on this list. That’s it! You can go in order or skip around—whatever feels good for you! The key, Pochotna says, is to really pay attention to what your crush is saying and how they say it. “Amid the anxiety, it’s easy to stop listening as you plan your next move, but you must show genuine interest by maintaining eye contact, nodding, and providing feedback,” she explains. “If you make them feel valued, they're more likely to continue sharing."

To get the most out of the game, Boodram suggests using a 2:1 formula when asking questions. Basically, after they answer the initial Q, ask ‘em a follow-up to dig deeper and help the conversation flow.

For example: Imagine you're discussing favorite travel destinations, and your crush mentions loving Paris because they’re passionate about art. Following up with, "What's your favorite art piece you've seen?" not only deepens the conversation, but shows you truly listen—turning a simple chat into a moment of real connection. Just be mindful that some topics might be sensitive, and not everyone opens up at the same pace. If someone doesn’t want to answer something, just move on. There’s plenty to learn while still respecting each other's boundaries, y’all.

21 Questions to Ask Your Crush

These questions are a mix of funny, flirty, deep, and casual topics. You can still touch on many different areas while keeping things fresh and fun. If you run through the entire list, make up your own questions, or switch to a game like Truth or Dare or Never Have I Ever to keep the momentum going. Who knows? A simple conversation game might just open the door to a lifelong love match.

  1. What movies or TV shows have you been obsessed with lately?

  2. Dog person, cat person, or neither? Why?

  3. How would you spend your dream weekend if money and time were no object?

  4. What’s the most unforgettable concert you’ve ever attended?

  5. If you could pick any place in the world for a vacation, where would you go?

  6. What’s a book or article that really made you think recently?

  7. What’s a song or album that you can listen to on repeat?

  8. What’s your go-to comfort food and the best place to get it?

  9. Where in the world do you feel most at home, and why?

  10. What’s one thing you’re deeply passionate about?

  11. Can you share an experience or person that has significantly shaped who you are?

  12. How do you define friendship, and what qualities do you value most in your friends?

  13. If you could learn one new skill or hobby overnight, what would it be?

  14. What’s the weirdest impulse buy you’ve ever made?

  15. If you could have a podcast with any celebrity, who would be your co-host, and what would be the main theme?

  16. What’s your secret talent that no one knows about?

  17. If you could switch lives with one person for a day, who would it be?

  18. What fictional world would you love to live in for a week?

  19. What’s the most daring thing you’ve ever done?

  20. If you could invent something that would make life easier for people, what would it be?

  21. What’s one question you’ve always wanted to ask on a date but never have?

You Might Also Like