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15 Messages To Send An Old Dating App Match If You Want To Try Again


Here's the problem with dating apps: It can be seriously tough to keep track of all your conversations. When you're juggling a dozen different convos with different matches, a promising one can slip through the cracks, and if too much time passes, messaging them again just feels awkward. Resurrecting an old convo is hard, but coming up with messages to send to an old dating app match is even harder. How exactly do you say, "Hiii, remember me?" without totally weirding out that long-lost match?

Maybe you talked about going on a date but never did. Maybe you actually went on a date but never followed up about a second. Maybe the word "date" was never even mentioned, but you two had what felt like a really great rapport before the conversation fizzled out. No matter how much time has passed since you last spoke, there are ways to revive a lost connection, so no need to kiss that potential relationship goodbye just yet. Whether the approach you take is a little self-deprecating or majorly forward, resurrecting an old convo is worth the risk. After all, that match may be hoping to hear from you again just as much as you want to message them.


It's OK to acknowledge that you feel a little awkward. But you can also smooth over the awkwardness with humor. A funny message will not only remind your match that you exist — it will remind them why they spent time talking to you in the first place. If you want to make your match laugh (and jog their memory about who you are at the same time), then try one of these playful messages:

  • [Sent along with a cute selfie] "In case you forgot what my face looks like, here it is. In case you forgot what we were last talking about, look at the convo above. Shall we pick up where we left off?"
  • [Sent in two different messages] "🚨🚨🚨." "Sorry to alarm you. It was the only thing I could think of to get your attention."
  • "Previously on Tinder, [your name] and [their name] were discussing the possibility of getting tacos together. On this week's episode, will it actually happen? Stay tuned to find out."
  • [Sent in two different messages] "Hey." "It took me [however long it's been since you last spoke] to come up with that message."
  • "🙋. Just popping up to say hi."

The best defense when something feels weird: Pretend that it didn't happen. Trip over a crack in the sidewalk? Strut away like you're on a catwalk. Allow 10 days to pass since last messaging a match? Act as though no time has passed at all. You don't have to acknowledge the fact that it's been a while since you and your match last chatted if you simply strike up a convo. Here are a few ways to get back on your match's radar:

  • "So how did that presentation you gave at work end up going?"
  • "I watched that episode of The Office we were talking about earlier and thought of you. How are you doing?"
  • "The weirdest thing happened to me yesterday, and I think you'll appreciate this story."
  • "Remember that burger restaurant we were talking about? They just added truffle fries to their menu, so now we definitely have to go."
  • "I finally read that book you recommended and we need to discuss."

Why beat around the bush? You two already wasted enough time that could have been spent dating! Rather than be cute or casual, be clear with your intentions. You're interested, you regret letting your convo go by the wayside, and you're looking to get those sparks flying again. If you're feeling bold (or simply impatient), then go ahead and send one of these messages:

  • "I realize it's been a month since we last chatted, but I feel like you're one of the good ones and we should keep talking. So what have you been up to this past month?"
  • "I know we talked about going on a date, but I think it's time we finally do it. You pick a time and I'll pick a place."
  • "Long time no talk! It feels like a shame to let this good convo die, so let's catch up."
  • "I've been wanting to say hi for a while now and I've decided to finally just do it. So hi."
  • "Clearly I'm terrible at keeping conversations going, so how about we continue this chat in person?"

Don't spend your time mourning the one that got away. Go ahead and send that old match a message instead. The worst-case scenario is that they don't answer, so the only thing you have to lose is a potentially great match.