I [M] matched with my ex’s best friend [F] on a dating app

I’ve been single for a few years now after I broke up with the most serious girlfriend I ever had, we’ll call her Jenn. She’s a great person, but we were young and I didn’t know what I fully wanted out of life yet, so I left and moved across the country for the last little while. Cut to today I’ve moved back to where we’re originally from, shes in a new relationship and I’m genuinely happy for her.

Being that I’m single, I fired up the dating apps and started swiping. I’ve never really had a ton of success on these apps but with covid, it’s been the only way to meet new people. About a week ago as I was swiping through, I saw a familiar face, my exes best friend, let’s call her Emily. I’d always found Emily incredibly attractive and I’d be lying if I said I hadn’t fantasized about her countless times, but being the childhood best friend of my ex, I thought those fantasies would remain just that. I decided I have nothing to lose and swiped right on her and I went about my day, the next morning I woke up, checked my phone and saw I had a new match and sure enough it was Emily.

For this specific app, the women have to message first before the conversation can begin and the conversation went as follows

Emily: Well this is awkward ?

Me: lol well I didn’t think you’d actually swipe right on me, considering my history

Emily: well considering I’m Jenns best friend, I didn’t think you’d actually swipe right on me either…

Me: I mean I always thought you were hot lol Do you think Jenn would be mad that we matched on here?

Emily: obviously! She’d be fucking pissed

Me: secrets can be fun ?

Emily: I always knew you were a piece of shit lol

Me: I’d agree with you if I tried this while I was still with her, but it’s been years, she’s moved on and the way I see it we’re two single adults, we can do what we want

Emily: and who said that’s what I want?

Me: So you never thought I was cute when I was with Jenn?

Emily: I mean she’s my best friend, of course we’re going to have similar tastes, but she’d kill me for even talking to you, let alone hanging out with you.

Me: it’s not like I’d tell anyone if we hung out, do you think I want to deal with that shit storm? Like I said before secrets can be fun lol

Emily: you’re bad ?

Me: what are you doing tomorrow night?

Emily: I have no plans as of yet

Me: well I think it would be great to catch up, you should come by my place

Emily: come to your place to catch up? You’re a smooth one ?

Me: just to catch up, nothing more nothing less lol does 7:30 work for you?

Emily: you’re actually crazy, but fine, I’ll come “catch up” with you, but if you tell a soul you’re gonna fuck my life up, so you better bet I’ll do the same to you if anyone finds out.

Me: I’m willing to take that risk lol ?

From there we just went over the logistics of things, where I live and such. This conversation happened yesterday and she’s coming over tonight. If there’s any interest in this post I’ll be sure to post an update on how the hang out goes.

Source: reddit.com/r/gonewildstories/comments/npc3c9/i_m_matched_with_my_exs_best_friend_f_on_a_dating

61 comments

  3. Well it is not uncommon to meet someone you know via another person. No hard feelings. Have fun!

  7. She’s interested. Ever after what her friend said about you during the breakup, if it doesn’t happen you somehow fucked it up.

  9. If you want it to be extra naughty, you can call up Jenn while Emily’s over just to say hi.

  10. Saving this, you better update sometime tomorrow.

    Genuinely gave me a smile, probably looked like ?

  15. >Emily: you’re actually crazy, but fine, I’ll come “catch up” with you, but if you tell a soul you’re gonna fuck my life up, so you better bet I’ll do the same to you if anyone finds out.

    What is she going to do? Tell Jenn? LOL! Godspeed, sir.

  27. I know what’s gonna happen! I just wanna know in what way and order! :)

  34. The setup for this makes me laugh. I personally don’t get why people are “not allowed” to date if they’re two single legal aged adults. In the queer world the dating pool is much smaller (tho for me it’s actually bigger lol) so everyone is mostly fine with dating your ex’s best friend. Granted the real reason is pure jealousy. But it still boggles my mind.

    But I will say secret dating does make things spicier, so yeah hurry up with part two! ???

  39. Wishing for the best! I hope you didn’t get too excited and made this post. Hoping your “catching up” goes smooth.

  44. I’m so fuckin interested that I’m willing to keep my fingers crossed hoping she does show up at your place, and everything happens as smoothly as all of us in this thread are anticipating.??
    Eagerly waiting for update..

  45. Makes sense you’d be attracted to your ex-gf’s best friend; like she said, you both have similar tastes. You’ve been broken up for a long time so there’s no expectation you wouldn’t see others. See how it goes but don’t keep it from your ex-gf from too long. There’s really no reason to given the circumstances. You’re not cheating and shouldn’t feel or act like you are.

  46. Can’t we just tell a fucking story around here without baiting everyone?

  53. Shouldn’t this be posted in “I’m hoping like hell this ends up being a gonewildstpry”?

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