I’m younger than many here, and also a “late bloomer” of sorts. Never married, and didn’t start dating until well into my late 20s (40 now). Despite that (or maybe because of it), I’ve been fortunate enough to have never been in what I would call a “bad” relationship, and have been in several good (if short) ones.
First ex was a long-distance relationship, on and off for about 1.5 years. She was much more experienced and ambitious (in terms of work, life, finances and so forth), so not a good romantic fit. I always felt not quite good enough (not in any sort of demeaning way, but just wanting different things out of life). The long distance also made it difficult to have any sort of normalcy. We’re still good friends to this day, though, and they recently transitioned (genders), which makes it interesting… my ex, yes, but also just another dude I hang out with? In any case, that was a lucky first breakup experience for me. No drama, no fighting, just two kind people who gave it a shot and realized it wasn’t quite what either one wanted. No regrets there, and it was very informative (and formative) in terms of shaping future breakups — they don’t always have to be a sordid affair.
Second ex was much more compatible personality-wise — she was a gentle soul, and we both loved music and nature — but she was very much on board the baby train and I very much was not. We’d only been seeing each other for a few months when she bought a house and invited me to move in with her. But I sat her down and had a nice heart-to-heart, and though we were both a little sad about it, breaking up was the right thing to do. She wanted to settle down with a family and I wanted adventure. That was never going to work. She soon met an older gent, an administrator at the school she taught at, and they had a baby not long after. I kept in touch with her for a few years after that, and last I heard, she was living a reasonably happy life as a surburban mom. We gradually fell out of contact after that.
Third ex was an incredibly passionate, intelligent, and politically astute lady I met at a protest. She was the one who made the first move, and we dated for a couple years. I liked her a lot and really enjoyed her company, but the romantic spark was not quite sufficiently there for me — something I did not realize until far too late. One day we were supposed to go out to a protest together, but she wanted to stay in for some us time, and that led to a whole discussion and then an argument and then a lot of crying and finally a breakup, all in a few hours. I ended up breaking her heart by admitting the insufficient attraction on my part. In hindsight, she must’ve felt like I was leading her on for months and months… something I never intended to do, but didn’t have the self-awareness to catch early on enough. She never talked to me again after that, and I can’t blame her. I wish I could’ve handled that whole thing better… not just the eventual break-up, but probably the entire relationship before it. I was always a bit lukewarm about it, but she was so into it that she talked me down every time I tried to bring it up. I should’ve been more insistent, earlier on, and not just let it keep going. It was hard since I did genuinely enjoy spending time with her, but it just didn’t feel right romantically.
Fourth ex was a foreign doctor who I met while she was visiting the U.S. for a medical conference. A few drinks turned into a night together turned into a few months of back and forth flights, with her visiting me and me flying over to visit her. She was an extremely intelligent woman, an accomplished doctor who owned her own little downtown penthouse apartment outright in a beautiful Nordic country. Her wealthy yet laid-back (by U.S. standards) Nordic lifestyle also afforded her ample vacation time, which she’d use to travel the world on exotic adventures, on horseback and with scuba fins and everything in between. Despite all this, she was generally not a happy woman, and the lack of a long-term stable partner fed into that unhappiness and vice versa. This was the only time in my life where I had my intelligence seriously questioned, which was (not to brag) pretty unusual for me — it’d just never been an issue in previous friendships, relationships, education, or careers. It never bothered me, but she brought it up a few times. More in a curious way than judgmental, but it still struck me as odd. In time, I’d come to realize that was her primary avenue of interacting with the world and its people. Whereas both myself and my previous exes & friends were emotional and sensitive people first (regardless of our intelligence), she was predominantly intellectual, and mostly related to others in that way. We would talk for hours and days about politics, history, NATO, economics… she was essentially a physical embodiment of the SDMB in that regard. But we were never quite able to form and sustain that level of emotional intimacy that a relationship really needs. Perhaps in time we could’ve, but the long distance again made it difficult. It eventually just petered out and we sadly lost touch over the years. I’d really like to reach out to her to rekindle a friendship, at least, but I’m worried about that being misinterpreted as romantic interest…
All in all, I’d just consider myself to have been very lucky. And I wish I could’ve known how to treat them better, especially towards the end of those relationships. Alas, some things I only learn through time and hard-earned experience.
Fast forward to the present day, and I’ve been with my partner for just over 4 years, and this one’s a keeper 
She’s very different from all my previous exes, but turns out to be exactly what I actually needed in a relationship (and hopefully vice versa). And with that, time to wind down this too-long post and go get breakfast with her…!
