Bold questions are great flirty questions to DM your crush
12 Flirty Questions To DM Your Crush When You're In The Mood To Chat


As the wise Nicki Minaj once said, "It go down in the DM." Sure, a double-tap on your crush's latest Instagram post or a like on their Facebook or Twitter updates might put you on that person's radar. But if you really want to make your interest known, sliding into the DMs is the way to go. The question, of course, is what exactly you should say (and no, I don't recommend a simple, "Hey"). If you want to get a convo going, then I've got some flirty questions to DM your crush that will definitely let you get your flirt on.

Here is a just a brief collection of the recent DMs I've received on Insta that wouldn't have worked even if I wasn't in a relationship: "Msg me back pls." "Marry me." "💝💘💕💖😻." And my personal favorite: "I want to get you pregnant." #NOPE. Sending a direct message to your crush might feel like a risk, but it can actually work if that DM is just the right amount of flirty (rather than, you know, something that might make your crush block you for life). Here are a few coy questions to pose to that cutie to get the ball rolling.

Teasing Questions

Perhaps you just want to test the waters. Hitting up a crush's DMs is scary, after all, so there's nothing wrong with easing yourself into the convo. Here are a few questions that will pique that person's interest but that won't leave your ego bruised if you don't get the desired response.

  • "So I see that you're a Yankees fan. Would the fact that I root for the Red Sox keep you from talking to me?"
  • "Not going to lie, your tweets always make me laugh. Can you promise to keep that A+ content coming?"
  • "I just saw in your Instagram Story that you were at my fave bar last night. Why haven't we ever been there at the same time?"
  • "OK, your dog is amazingly cute. What's his name? (You're also not bad looking yourself, BTW.)"
Bold Questions

If you want to make things happen between you and your crush, it might be time to pose a question that makes your intentions clear. Remember: Fortune favors the bold, and boldness can pay off in a big way.

  • "Someone certainly looks like they've been hitting the gym lately. How about you become my personal trainer?"
  • "That red shirt is seriously working for you. Have you considered buying it in all colors?"
  • "I'm loving your new haircut. Are you trying to impress anyone in particular or just me?"
  • "Could you please post pictures more than once a month? I'd really like to see more of you (both on my feed and IRL)."
Full-On Frisky Questions

Ready to dive in head first? You can tell that object of your affection exactly what's on your mind with a totally titillating question. You might be putting yourself on the line with these provocative inquiries, but isn't that what sliding into the DMs is all about?

  • "I couldn't help but notice that you liked my latest bikini pic. Should I post a few more?"
  • "So you like all my posts but have never even asked for my number. If I give it to you, can I expect you to text me soon?"
  • "Is it weird that ever since you posted that last pic I can't stop thinking about you?"
  • "I've never seen an SO in any of your Insta photos. Is it safe to assume you're single?"

Just to be clear, consent applies to direct messages just like it does to IRL sexual behavior. While you definitely don't want to make your crush uncomfortable, sending a flirtatious DM question is a great way to make a first move — and if your crush is into it, who knows what might happen next?