11 Questions To DM Your Crush That Feel Natural, Not Cringeworthy

Common interests are a pretty safe bet. Whether they posted a cute pic of that coffee shop by your house or went on a gorgeous hike, try making a simple connection about something your both have in common. After making said connection (i.e., "I live right by that place!"), ending your message with a short question like "What's your favorite thing to order there?" can really open the conversation up in a mellow way.

Sending a DM about something your potential boo is currently doing can be a super low-key way to connect in the moment. If your crush just dropped a cute pic of themselves out on the town or they posted a story about seeing a live band, ask them how their night is going or inquire about their plans for the rest of the evening. Replying to their story or engaging with some of their recent posts may help you feel more comfortable sliding into those DMs, baby.

If you just moved somewhere and you're still figuring it out, asking your crush for their food or venue recs can be a super sweet way to start a conversation. Of course, no matter how long you've been living somewhere, there's always more to learn about your city! Ask them about where they always get their bright sneakers or where their favorite burrito place is.

OK, if they literally tagged the location, you may want to come up with something a little more creative. Still, asking about a recent trip they took or even a #TBT post of a trip they took at some point is a great way to start a conversation. Whether you also love to travel or you just want to know more, asking them about the places they've traveled to can be sweet and low-key.

First things first: You should never keep tabs on or follow a crush around. You need to respect their boundaries. However, if you semi-know your crush, you've met in passing, or you both follow each other, making that connection can be really sweet. Whether you talk about your favorite thing to order or share a funny story about an interaction you had with the cashier, talking about a place you both love is a built-in connection.

While sending just a meme can be a move, sending a meme with a witty question like, "Is this not our friends when the train doesn't come?" opens the floor for them to respond. It also takes the pressure off of saying something funny, because you beat them to it. (Go you!)

I think the adult version of "My mom says I can't go!" is dropping, "Our mutual friend says we should hang out." Asking about a mutual friend or trying to plan something around someone you both know can create a mellow group-hang in which you and your crush are both in attendance.

If the gym you both go to is having an event or the local coffee place has new seasonal flavors, sending them a post that made you think of them and asking a question about it is a super thoughtful way to get the conversation going. Of course, if you're ready to drop in a, "let's go to this together!" just saying, "Did you see this?" can let them know that you're thinking about them, but in a very chill way.

Perhaps my favorite way to ask someone out: State something that you were already planning on doing and casually extend an invite. If you don't know your crush that well jumping in their DMs with a, "Let's go on a date!" may feel a little fast (or not! You do you!). Inviting them out with your friends is just a friendly thing to do. Ending with a question like, "Do you want to come by?" opens up the convo to chat more.

If your crush always posts pictures of their impeccably clean room or they seem to find the cutest coffee places, asking them about how they do it can be a silly and creative way to start a conversation. Whether you ask about where they like to shop for sweaters or how they always manage to find the prettiest places to watch the sunset, you're sure to learn more about them in a cool way.

The other day I got a DM from a cutie I went to college with. They sent me a picture of a highway sign with my hometown on it, accompanied by the message, "Hey, aren't you from Swampscott?!" They were driving through Massachusetts and happened to pass by my town. Though it was a purely platonic DM (I think? LOL), the gesture was incredibly sweet and made me feel super good. Someone remembering something little you told them once is the best feeling ever. If something makes you think of your crush, sending it over and asking them about can say, "Hey, I like you, and I remember the things you tell me."

If you're crushing on a cutie, sending a sweet and natural Instagram message can be a really mellow way to get the conversation rolling. Whether you ask about their latest post or send them something you think they'll like, going down in the DMs can be as low-key as you want it to be.