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20 Clever Questions To DM Your Crush To Get The Conversation Going

On Sunday, I opened Hinge and instantly matched with a brunette named Caleb.* He immediately asked me for my Instagram handle, and I happily shared it. Soon after, I got a DM: "Do you want to grab drinks sometime soon?" We agreed to get together on Tuesday, but despite my initial excitement, my interest soon withered. I later realized what had happened: Our conversation was no longer stimulating. So, I came up with 20 clever questions to DM your crush right then and there, so that you never bore the heck out of someone you're crushing on.

Don't get me wrong — learning the little things about someone new can be a vital part of developing any sort of a close relationship. But before diving into the nitty-gritty, I suggest you use social media to your advantage by asking some intriguing questions first to elicit excitement. In order to take your convo from sliding into the DMs to meeting up IRL, you'll have to establish a certain amount of chemistry. So, when you send that first message, do so with gusto — so sparks can fly.

Read on for a list of unexpected questions to DM your crush, from the carefree one-liners to the deep-dive conversation starters.

1. Lighthearted Questions

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1. Which song is the perfect soundtrack to your current life?

2. What's one new thing you learned this week?

3. How would a parent describe you? (Don't pull any punches!)

4. Do you prefer a giant house in a subdivision or tiny house somewhere with a view?

5. What's the last book you really loved?

6. What's the New Year’s resolution you always make but fail to follow through?

7. Who would play you in a movie? (This would be a great response to a photo of a celebrity they posted to their Instagram story.)

8. What futuristic movie do you think the future will resemble?

9. What's your favorite meme?

10. What's your go-to video when you need a laugh?

11. How many of my questions do you think you could answer in just photos?

12. What are your go-to 'Two Truths And A Lie' answers?

2. Personal Questions

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13. If tomorrow was your last day on earth, what’s one thing you’d really regret never having done?

14. Who knows you best?

15. Where's 'home' for you?

16. When's the last time you cried?

17. What's your dream destination to travel to?

18. What event has changed the course of your life the most?

19. How do you calm yourself down when you're upset?

20. Where do you think you'd most enjoy living?

Once you get the conversation rolling and feel comfortable enough to take it even further, you might consider asking them one more question: "What would you say if I asked you out?"

*Names have been changed.