Why Does He Keep Failing At Relationships?

Hello, Doc.
I’m 27 years old guy. Lately, I’ve been trying to comprehend my feelings about my last two relationships and setting my boundaries. I’ve always had low self-esteem with all that it implies. No firm boundaries, conflict avoidance and so forth. I’m working on improving my lifestyle and with the changes comes confidence. The only thing that leaves me confused is romantic relationships.

Last year I was dating this girl, May. Mostly out relationship was great. We had similar life positions, we took interest in each other’s hobbies and we hated the same things.

But.

Sometimes she would get really pissed at me for various reasons. Sometimes she would interpret my words or actions in a weird way, like I was trying to be covertly rude with her, other times…I don’t even know…bad mood? When she didn’t like something, she would lash out on me and say, in very unpleasant ways, that I don’t appreciate her. We dated for about six months in total and during that time she broke up with me three times. Every time she apologized shortly after the fight but refused to discuss it. After the third time we didn’t see each other for two months. Then we got back together, spend two weeks doing a lot of romantic stuff and having mind blowing, leg shaking sex (leg shaking for both of us, which was interesting). Until it happened again.

We were discussing our plans for the upcoming weekend when she said she wanted a surprise. I thought it was a cool idea. I said that I too want a surprise. She got mad. I did my best to defuse the situation and it turned out she thought that I meant some passive-aggressive shit like “Oh, I want many things too, honey!”. My idea was that I’d make something for her on one day and she would do something for me on the other. Sometimes I want to be treated like a queen too, you know. I decided that it was time to call it quits and thanked her for the good times. I know, I’m describing her as my crazy ex, but I can put my hands and my heart on the Necronomicon and swear that she is a cool and smart person and it really saddens me that our relationship didn’t work out. I guess we expected different things from each other.

Then there’s July. I dated her before May, about two and a half years ago. It was a hard case of oneitis. I adored her immensely. I had a crush on her since the first time I saw her. After two years of admiring her from a distance I asked her out. We dated for 5 months, she broke up with me and told she wanted to be friends. That was heartbreaking but I tried my best to stay cool. It was very hard to move on, as we are co-workers and I see her every day. But we actually became friends. Not close friends, but still. Over time, though, I started realizing that she’s not that great of a person as I imagined she is. She’s good and caring and all. But I feel like she’s a little resentful, a little tactless and a little manipulative. I say “a little” because usually it’s very subtle, only noticeable by her snarky, out of place or passive-aggressive comments, said under her breath every now and then. It’s subtle and I’d usually pretend I didn’t hear those remarks, but they were enough to make me have bitter-sweet feeling every time we met. Happy to see her but waiting for it to be over.

During the past holidays I fell into depressive mood and didn’t want to see anyone. I only met with my closest family and spend most of the holidays playing videogames with my best friend whom I haven’t seen for months due to life reasons. When we got back to work, it looked like July was avoiding me, keeping her eyes down when walking past me and when our eyes did meet, she would immediately turn away. I texted her to meet me at our usual secret meeting place (we kept our relationship as secret as possible), as I wanted to give presents for her and her daughter. But she replied to me asking why I was so eager to see her all of a sudden, after so many days! That’s where my admiration with her has ended. It was so unexpected and odd. I assume she expected me to reach out to her during the holidays and got offended when I didn’t (except the short exchange of congratulations). But we are not that close to spend all the time together and we met at my place just a few weeks ago. So, I told her that I didn’t insist on meeting and that was the last time we talked. I was thinking to call her if not to restore our friendship then to make peace, at least. I just couldn’t bring myself to do it. I don’t hold any grudges against her but I don’t want to have her in my life either because relationship with her is not that enjoyable, and it hasn’t been for quite a while.

And here I am, trying to get closure. I learned how to cut people from my life, to stand my ground and not fall into abuse. I don’t have the need to explain my positions in life and just do my thing. That, in turn, means that I’m closing myself from people even more than I did in the past. And potentially remove the possibility to connect with people who might be right for me. What if I was at fault in these two relationships? What if I wasn’t attentive and caring enough? Was it just incompatibility or my inability to adapt and compromise? Surely there was something wrong and stupid I did, I’m a human being after all, though I never mean any harm and I try put a lot of effort into relationships, which makes it even more frustrating. I’d like to pursue a new romantic relationship but I’m afraid I’ll fuck it up with my ignorance.

At this point I will appreciate any advice. Thank you.

Drizzle is a Lifestyle.

It’s good to examine your past relationships and try to see what you can learn from them, DIAL… but that only works if you are taking the right lessons from them.

Right now you’re taking two radically different relationships — and equally reasons why they ended — and coming to the conclusion that this was all your fault and that you must have done something wrong to have been dumped twice. But what you’re failing to factor in is that you don’t actually have the complete control that you seem to think you did. Occasionally relationships will end because of things that are entirely outside of your sphere of influence. There will be times, for example, when events that are completely external to your relationship will cause your partner to decide that she might be better off being single right now. To give a personal example, I’ve had relationships end twice because of deaths in the family; in both cases, deaths of someone close to them prompted the women I was seeing at the time to reevaluate their lives and decide that they just couldn’t handle being in a relationship at that time. Which sucked for me to be sure, but there was nothing to be done; there wouldn’t be any amount of caring or effort that would’ve changed their minds.

Other times, the problem won’t be something that you can fix or work around because it will be a flaw inherent in the relationship. Such as, say, dating someone who apparently has a massive chip on her shoulder, keeps lashing out at you whenever she gets a wild hair up her ass and otherwise treats you like an emotional chew toy. The lesson you should be taking from this one was that bed-rocking sex isn’t going to make up for someone treating you like shit. The mistake you made here wasn’t that you didn’t love May enough or compromise enough, it’s that you were putting up with  someone treating you badly. This was a relationship that should have been over long before you got to the third break-up. As cool as you insist this woman was, the way she was treating you was unacceptable, and the cycle of “break up, get back together, get dumped again” should have been a warning.

Your relationship with July is another example of ignoring your feelings and keeping a relationship going because… well, I’m not entirely sure why. But the fact that you wanted things to be over whenever you were hanging around her was yet another indicator that hey, maybe you should just cut ties and call it good. When being around someone sucks the life out of you, makes you feel lonelier than if you were actually on your own or otherwise makes you watch the clock because you can’t wait to leave… those are all signs that it’s time to go.

Still other times, the issue isn’t what you did as much as what you didn’t do.In the case of your relationship with July, it’s the fact that you didn’t communicate with her the entire time you were out for the holidays. While yes, you were having a depressive event, she didn’t know that. All she knew is that you’re radio silent for weeks, and then suddenly you were up in her business again. To her, that almost certainly looked like a relationship that was ending, without even the courtesy of being told why. Once you were back in her life… well now she has no clue just what’s going on, and ample reason to be annoyed at you. If this was a relationship — platonic or otherwise — that you wanted to maintain, giving her a heads up that you were in a low place and probably going to be a hermit for a while would have been the smart move. Not talking to her at all for days or weeks, then acting like nothing happened is a great way to annoy people.

The bigger takeaways here shouldn’t be about how you failed these relationships and more the recognition that these relationships were not right for you. Rather than worrying that you weren’t attentive enough, focus on finding people who are in good emotional order and who make you excited to see them. When being around someone is making you miserable, then that’s a sign that you’re in the wrong relationship… no matter how great the sex is.

And don’t just quit talking to someone with no warning if you actually want to keep a relationship alive. It just looks like you’re trying to ghost them.

Good luck.

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