Bit of a different question here, but I’d really appreciate some perspective.

I ended a 14-month monogamous relationship roughly a month ago. I’m 28M, she’s 23. On paper, the relationship was almost perfect. She pursued me from the start, looked to me as the leader, and constantly supported me. She gave thoughtful gifts, cooked meals, showed genuine interest in my life, sent daily texts/videos, and gave her all in the relationship. She’s warm, funny, affectionate, beautiful, and one of the kindest people I’ve met. My family and friends loved her too.

For context, I’ve dated a fair amount (50+ first dates, around 6 serious relationships, multiple flings), so I’m confident this isn’t “first love” infatuation. Normally, I’m the one who ends things, and usually I feel instant peace when I do. But with her, I’ve broken up twice (once at 4 months, and again after 14 months) and both times I’ve almost immediately felt like it was a mistake.

There was nothing obviously wrong. I just didn’t feel 100 percent certain she was “the one.” I never cheated or pursued anyone else, but I did sometimes think about other options. I know I can get “shiny object syndrome” in other parts of life, so I’m not sure how much weight to give that. Eventually I thought, if I’m still on the fence after this long, maybe I should end it rather than drag it out. The tricky part is that she would have married me in a heartbeat, and deep down I could absolutely see her being the mother of my kids.

Another factor is that she lives in a small town, runs her family business, and her dad has cancer. For me, small-town life feels suffocating. She was open to long distance, but I didn’t give that option enough thought before ending things.

Here’s what’s throwing me off. After the breakup, instead of peace, I’ve had sleepless nights and regret that hasn’t gone away. It feels like I might have made the wrong call. Recently I learned about attachment theory, and avoidant attachment describes me almost exactly. Since my first heartbreak at 18, I think I’ve developed a defense mechanism where I pull away when things get serious, even with someone great. Reading about this was eye-opening.

So I guess my questions are:

  1. Is attachment theory legit, and if so, how do you work through avoidant patterns?
  2. In this situation, would it make sense to try again with her, or would that just repeat the cycle?
  3. People say the “right relationship” feels effortless and obvious. But if I’m avoidant, maybe it never will for me, even if the person is right?

I know I’ve hurt her by breaking up twice, and I’d hate to do it a third time. I want the best for her and don’t want to waste her time. But I genuinely miss her on a deep level and could see an amazing future with her. I just dont know if the fact that I’ve already ended it twice is proof enough that it’s not right.

Would really appreciate any honest outside perspective.

TLDR: Ended a near-perfect 14-month relationship twice. Both times felt instant regret instead of peace. Learned I might have avoidant attachment. Struggling to figure out if I should work through it and try again with her, or accept that ending it twice means it’s not right.


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