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Why Does He Keep Failing At Relationships?

February 10, 2020 by Dr. NerdLove Leave a Comment

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.


Hello Doctor,

I’m a 35 y/o woman with very little experience in relationship with men. I’ve only been in actual relationships 3 times in my life, and one of them was a complicated 3 years relationship with a married man who wasn’t completely available.
I don’t find it difficult to be without romantic relationships on a day to day basis, and I honestly don’t brood about it; I’m not one of those people who are always preoccupied with dating and I don’t feel like it’s a necessary part of life. It’s nice when it happens, but I find it very hard to get attached randomly to men. The past relationships were ones who grew out of friendships and long terms acquaintances.
I do have a long history of crushes on friends who never came to anything because I was too shy to confess about my feelings to them.
I never have sex outside of those relationships, and in that context I’ve learnt about the term Demisexual in the past year and I feel like it applies to me – though I am interested in sex, I don’t see myself having casual sex with people I’m not attached to.
I do have a pattern though that had been bothering me for a while and I’m too ashamed to talk about; I have a tendency to develop a crush and what even feels like strong feelings towards celebrities. It’s been happening for years – every once in a while I develop a crush on an infatuation with a certain celebrity (musicians, actors) who’s external personas seem to be exactly “my kind of guy” and in my head I enter periods of imagining how I meet them and begin a long term relationship with them. I admit those infatuations can last months and they tend to occupy my free time in my head. It doesn’t bother my day day, rather happens inside my head in my free time. These thoughts give me a chance to imagine meeting someone and being intriguing, desired and sought after. The ‘relationships’ I build with them in my head are good ones and I suppose are a reflection of of the type of relationships I’d like to have if I would ever find myself in an exciting situation where a super interesting, attractive, (famous?) person find me attractive enough to pursue a relationship with me. It usually ends because the infatuation is over, I suppose.

I never stalk, online or offline, or make any attempts to contact these celebrities. I live outside the US so it’s not like I can see these people randomly on the street. It’s very clear to me that these people are very different from their external personas and live their own lives. It doesn’t mean though that I don’t get a jealous twinge if a paparazzi photo shows they’re dating someone new. However, in my very rational, down to the earth part of the brain, I understand it’s silly and I’m even ashamed by it all – to the point I’m reaching out to you through an alternative email address.  I’ve even been ashamed to admit this to a therapist I’ve been going to for a while to discuss, among others, my difficulty in bringing myself to take steps towards finding a relationship.

I will add that “imagining” these relationships isn’t something I do in context of celebrities only; I mentioned having numerous crushes and it always happens when I have a crush on someone too. In my head I build a story for us, like a movie, where everything goes great and everyone’s happy.

I guess my question is – well, is it weird? Do you think this is a bad habit, something that’s worth getting rid of? Is this something that I should worry about? I feel it does give me some sort of comfort in relation to the fact that I don’t have actual romantic relationships, but the question is – should I feel guilty about this?
Thank you,
Imaginary (Boy)Friend

Crushes on celebrities and strangers is normal, IBF; we get them all the time. All it means is that you’re a mammal with a sex drive and an active fantasy life. The fact that yours are fairly elaborate and detailed is, likewise, not terribly unusual. You’ve got a vivid imagination and you’re playing out pleasing scenarios in your head.

Of course, it doesn’t exactly take Dr. Freud to see what’s happening here. These fantasy relationships are just that: fantasies. They’re “safe” ways for you to explore potential attraction to people and — as you say — practice for the kind of relationship you’d like to have some day. Again: that’s not terribly unusual or even that rare. In fact, there’ve been studies that’ve found that imagining various scenarios that you’re expecting to encounter can help prepare you for them in reality. And playing out scenarios in your head is a great way to defang fears of things going horribly horribly wrong.

The only time that these fantasies could be a problem is if they’re interfering with your day to day life. If, for example, you’re using these fantasies as a way to avoid going out and pursuing real relationships, then yes, it can be an issue. That’s when it’s gone from “harmless fun” to keeping you from trying to live a life that you actually want. Similarly, if you’re conflating the emotion of the fantasies with real life and blurring the lines between fantasy and reality… that’s a horse of an entirely different color.

But it doesn’t sound like you’re doing that. It sounds like these are just pleasing distractions for you, a sort of emotional safety blanket. And honestly? That’s fine. if you’d rather have the fantasy relationship and you’re ok with your life as is, otherwise… well I don’t see any harm. It makes you happy, it keeps you satisfied and you don’t feel like you’re missing out on anything. You’re not confusing these scenarios for reality and they’re not bleeding into your non-fantasy life. It’s quirky, but it isn’t harming anyone and it makes you happy.

Plus, it’s happening in the privacy of your head. That’s nobody’s business but your own. If writing mental fanfic relationships between you and, I dunno, Orlando Bloom makes you happy then more power to you. The world has enough pain and chaos out there right now; enjoy these little nuggets of happiness all you want.

Good luck.

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