How To Start An Engaging Conversation With Someone On A Dating App


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Anyone can send a message on a dating app, but how do you start an engaging conversation that might actually lead to a real-world connection and/or date? Maybe you finally matched with someone who looks interesting, or you’re on an app like Bumble, where the lady has to kick things off. Here are the top 10 best ways to start talking with someone you match with on a dating app so you can see where things go.

Offer a specific compliment.

Pro tip: telling someone “you’re hot” doesn’t really cut it any more. Instead of a generic compliment that could be given to several different matches, try something a little more specific. “You have really nice eyes” sounds a bit more genuine than “you look nice.” Of course, if your compliment is too specific, you can always start by saying “I know this sounds a little weird, but…” Then go ahead and ask a question to keep the conversation moving.

Ask a question about their photos.

Pick something specific in their photos, like their jacket or the scenery, and ask a question about it. (“I love your jacket in the first pic! Where did you get it?”) You can also ask them about any pets in their pictures. This is a good way to show that you actually looked at their profile, as well as a chance to break the ice. Plus, if they tell you where they got their jacket, you can go buy one for yourself.

Don’t get mad if they don’t reply.

If somebody leaves you on read, don’t have a temper tantrum and start cussing them out through messages. Just send a nice, non-threatening follow-up message, keep it simple, and remember that sometimes people just forget to reply. You could rephrase your original message, or just send a gif. If they don’t respond after two messages, it’s time to move on.

If they have an unusual career or interest, ask how they discovered it.

The key here is to show how interested and curious you are, while giving them a chance to talk about something they enjoy. And if you also happen to share this common interest, say so! Shared interests are always a great way to form connections with people. Try something like, “I saw on your profile that you’re a professional basket weaver. I actually just started taking basket weaving classes! How long have you been making baskets?”

Try some light-hearted teasing and banter about their interests.

This works best with sports teams, favorite movies, and favorite restaurants. For example, you could joke with a Marvel fan about how DC is actually better. If you keep it super light-hearted, this is a great way to make sure they reply to you— after all, Marvel is way better than DC!

Ask a ‘would you rather?’ question.

Keep it positive (no picking between different ways to die!) and use it to start a conversation with someone who seems more fun or lighthearted. One of my favorites is, “Would you rather travel the world in a boat, or in an RV camper?” A bit basic, but it initiates the conversation. Best case scenario, they reply with their answer and then ask, “you?” So the conversation can keep going.

If they mention their sense of humor, send your cheesiest pick up line.

Then follow it up with a laughing emoji or something to make sure they know it’s supposed to be cheesy!

Ask for Netflix show recommendations.

Or movie recommendations, or album recommendations. The more you can connect it with their profile, the better. (Like asking a jazz fan who his favorite band is.) People love to talk about their favorite shows, movies, and music, and if he’s checking his messages, you’re almost guaranteed to get a response.

Send a gif.

According to DatingXP, sending a gif is the best way to get a response from somebody. It shows that you put some thought into finding the perfect gif, but it’s more visually interesting than a text message. Try sending a gif that says something a little more interesting than “hello.” Best case scenario, they send a gif back, and now you can hold your entire conversation through gifs, which is much more fun.

Just ask them out.

Last but not least, you can always skip the awkward first few messages and ask them out for coffee. It’s a great way to show that you’re actually interested in a relationship, and if they’re interested, they’ll reply to set up the date. Good luck on your dating journey!

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