AITA: I’m dating the same person for a third time.

AITA: I (23F) am talking to my ex boyfriend (22M) for a third time. We met early on in college and dated for a few months, with me being the original pursuer. I liked him and we had a connection, but I was not in the mindset to be someone’s girlfriend at that point in my life. We were young and I was not very emotionally mature and decided to end things with him after about three months. We didn’t get super serious, so I really didn’t think twice about it.

After I ended things with him, I continued to think about him constantly. I had reached out to him a year later to see if that door was still open and it was. We started dating again and got more serious this time around. Honestly, I hadn’t done much self reflection in between these periods and hadn’t matured a whole lot. That being said, after just three months again, I decided to end things with him because I didn’t feel like our connection was strong enough.

I genuinely cared about him and seeing how hurt he was after this breakup really made me realize that I was not someone who should be in his life. We stayed mutuals on social media and would engage with each other every once in a while, but we were essentially no contact for almost three years. Shamefully, I’ll admit that I thought about him A LOT while we were not together.

Fast forward to a couple weeks ago, I get a notification from Spotify that he had saved one of my playlists. As music was something we really bonded over, I reached out and asked him if he was enjoying my playlist. This was genuinely supposed to be a harmless gesture, but it snowballed into us meeting up again which then led to a huge conversation about why we keep coming back to this relationship. He confessed that despite us now living over two hours away from each other, he wants to give things another shot.

Am I the asshole for agreeing and giving things another go? I obviously have a difficult time making up my mind and being happy with my decisions, so a lot (if not all) of the problems between us are coming from my hesitation to fully commit myself to him and our relationship. I do like him and it’s VERY rare for me to find myself liking a man, so I want to take this as a sign that something good could come from this. But a huge part of me is scared that I’ll back out again and not just for myself, but because deep down I know that he deserves to be with someone who has zero reservations about being with him.

8 thoughts on “AITA: I’m dating the same person for a third time.”
  1. You should probably go to therapy first, so you can figure out why you keep getting cold feet about commitment before you risk breaking this guy‘s heart again. It sounds like you’ve got some fear or trauma or something going on there, because you like this guy so much that he’s been on your mind for 3 years, even though you were the one who pulled away. If you don’t figure out why you behaved that way and heal whatever it is that got you doing that, you’re likely to repeat that pattern. YWBTA to get romantic with him again before you’ve done the work to get yourself relationship-ready.

  2. YTA Stop torturing the guy. You are “the one that got away,” and that’s probably why he wants you. You both aren’t mature enough to end this circus. If you’re not ready to commit, don’t – you don’t love him, you were uncomfortable in the relationship with him, and you like him only because he makes you feel better about yourself.

  3. You dumped him, then you crawled back, then you dumped him again, then you crawled back again. YTA for dumping him twice. If you dump him a third time, then “ahole” wont even begin to describe what you are. Make this relationship work now. 

  4. Been there & done that. I even married him twice. He came around the second time to see if I was stupid enough to take him back. I was (damn it). I ended up leaving him again. I lost 200 pounds overnight when I drove away for the last time. He was sitting on the curb crying like a baby.

    Don’t do it. Don’t be like me.

  5. You ended things the 2nd time because you felt your connection wasn’t strong enough and that you weren’t someone who should be in his life. Which means you need to ask yourself what if anything has improved about you such that you would have a strong enough connection this go round. If you can’t name anything but go ahead anyway, then you would be wasting his time and YWBTA. And no, a saved Spotify playlist does not a strong enough connection make.

  6. Fool me once shame on you, fool me twice shame on me… fool me 3 times? I think he knows exactly what he’s getting into this time around.

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