‘How Do I Cope With Uncertainty and Lack of Control in My Dating Life?’

Q:

At 28 years old, none of my relationships have ever lasted to a year (either I or the other person recognized incompatibilities). I’ve dated people for short periods and had situationships, but I stopped doing the latter because it wasn’t good for me. I’m feeling depressed that I’ve never gotten to have the Valentine’s Day dinner, or the Halloween couple’s costume, or gotten to bring someone around to meet my friends and family. I get matches through online dating, and I get first or second dates, but then nothing. It is so demoralizing to swipe and match and message and then have nothing happen.

My Dad is getting married for the second time soon, and while I’m so happy for him and his fiance is amazing, I’m also envious.

I like myself, I like my life, I’m in therapy, I have hobbies, friends, etc. but it aggravates me that I haven’t been able to enter into and sustain a compatible romantic relationship. It is also scary to think that I might live for years or even the rest of my life as a single celibate person who has never had any satisfying sex or romantic relationship. How do I free myself of these emotions?

A:

This is the hardest kind of advice letter to answer, because on paper, you are truly doing everything right! Normally when people express disappointment and sadness about unfulfilling and short-lived romantic relationships, my advice is to invest in themselves and their friendships, but you are seemingly doing that. You’re in therapy, cultivating hobbies, have friends, etc. That’s all great stuff!

I think it’s worth naming something else you’ve done well: deciding to end relationships when (presumably unresolvable) incompatibilities come up. A lot of people, especially a lot of people in your shoes who really do want to have a lasting long-term relationship and never have, would ignore incompatibilities for the sake of continuing the relationship, which in many cases is the wrong thing to do! You’re making emotionally intelligent choices and ones that ultimately prioritize your overall well being. Because as I’m sure you know; it’s just about being in A relationship but in the RIGHT relationship for you. I also think it’s good you stopped pursuing situationships when you realized they weren’t good for you; I was never a situationship person either, so I get it!

I guess I wanted to give you some credit there just to emphasize that you’re not the problem. It’s an unfortunate reality that someone can be doing everything ‘right’ and still struggle to find long-term partnership. It is natural and understandable to be envious of your dad or of any other coupled up people in your life (especially any coupled up straight people, who yes do struggle with dating, too, but who don’t have to quite overcome as many societal and systemic obstacles as we do, not to mention the sheer numbers game of queer dating being more challenging).

There are so, so many people who are in the same boat as you. I hope some will chime in in the comments, even just to show you you’re not alone and to commiserate. I answered a similar, though inherently different since everyone is different, question a couple years ago from someone also struggling with dating in their late twenties; perhaps there are parts of their letter you can relate to. There are also some comments on that article from people in similar situations that I think are worth reading just to, again, show you you are not alone and help you feel like it’s okay to have the emotions you’re having.

You want to free yourself of these emotions altogether, but I also think it’s okay to feel them. Because if you’re already doing all the self-work, you’re right about this: There’s so much uncertainty and lack of control when it comes to dating and finding a long-term relationship. We cannot manifest a perfect partner. The online dating and apps are demoralizing, because they’re kind of designed to be! Their built with profits in mind rather than real, meaningful connection. That isn’t to say they’re worthless, but it’s certainly not just you feeling demoralized by the lack of progress using those platforms.

Just because your past relationships weren’t the kind of lasting, long-term love you wanted doesn’t mean those relationships were failures. Hopefully you learned about yourself and what you do seek in relationships. The dating game so often just amounts to a waiting game. Sucks, I know. I hope you find the love you envision for yourself. You deserve it; everyone does.


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Kayla Kumari Upadhyaya

Kayla Kumari Upadhyaya is the managing editor of Autostraddle and a lesbian writer of essays, fiction, and pop culture criticism living in Orlando. She is the former managing editor of TriQuarterly, and her short stories appear in McSweeney's Quarterly Concern, Joyland, Catapult, The Offing, The Rumpus, Cake Zine, and more. Some of her pop culture writing can be found at The AV Club, Vulture, The Cut, and others. When she is not writing, editing, or reading, she is probably playing tennis. You can follow her on Twitter or Instagram and learn more about her work on her website.

Kayla has written 1127 articles for us.

4 Comments

  1. I’m 32 and in the same boat, however I have chosen to avoid dating the last couple of years as a choice. When I make the opportunity to meet new people, I embrace it, but I don’t seek it. I guess my main advice for you is keep doing what you’re doing, or get out in the wild more, as apps just never did me any good. I have chosen to avoid dating because it’s what I need now, but you seem like you’re ready to find your person. Just enjoy what you’ve cultivated, make dating yourself a priority too, and when you’re out for coffee, or out for a trivia night with your friends, you can meet and get to know someone that could change your life. You have so much time, and it’s better for you to instead look to what you have (a great life it seems), and not what you’re missing.

  2. I can relate, and didn’t have any lasting relationships for most of my 20s, either.
    However, one thing that struck me was the writer’s repeated mention of compatibility. Because now that I’m in my second longer relationship, the question of compatibility comes up for me in different ways than it used to. It is still always something that needs to be weighed, and sometimes just faced head-on in ways that many of us avoid for the sake of staying in a relationship. But on the other hand, I’m wondering what exactly the incompatibilities are and how the writer has experienced the different stages of their relationships so far? We all go through phases of being head over heels, of being insecure, then gaining some security, then being disillusioned, realizing how different we really are, and then there is also an opportunity for a deeper getting to know each other, an acceptance of each other, a figuring out how it could work, what is amazing about the person even though they are (I would dare to suggest always) less compatible than they seemed at first.
    And I think these phases can be especially challenging for those of us (which is probably most of us queers) who have attachment issues, because those will come up in different ways in all those different phases, and sometimes things can feel enormously, overwhelmingly incompatible when actually there is a different, subconscious issue going on, some old wound that’s rearing it’s head. So cudos to the therapy! I’d be interested whether you can discuss those dating experiences and maybe your view and experience of compatibility and your attachment wounds with your therapist.

    The relationship I’m in is now 3 years old and I’m also, once again, in a serious re-estimation of how compatible we are, how I deal with my needs that are not being met, what needs ARE being met and what does that balance mean for me. And I’m realizing, once again, that these questions are alive and shifting as my partner and I grapple with them together. Some things I’ve really moved on to accommodate my partner, some things they’ve really changed in the last years to meet me better. Some things are still frustrating as fuck, and I can’t tell you for sure yet whether they will resolve or be a reason to split up in the future (because my own attachment issues mean that splitting up is generally at least close to the table, if not on it).
    So I don’t have a solution, but just wanted to share my little meditation on compatibility, because that’s an aspect that wasn’t addressed very much in the answer given.
    Best wishes to the writer!

  3. (I am making two assumptions here, because they were not specified: the person is gay, and the person is living in a place with < 1 Mio inhabitants. If that's not the case, ignore my reply.)
    When apps didn't exist, there were personal ads, and they were equally dysfunctional. Back then every queer knew that it's a numbers game and you have to move to a big city if you want to have any chance with dating. Todays online dating world hides the fact that the statistic chances for homosexual dating (not counting bisexual here for demonstration purposes) are still less than 10% of straight people chances.
    And this is not even calculating that queer people tend to cluster in very big cities, so that any smaller city has even less queer people than the statistic avarage of under 10 %.
    Dating while queer is basically dating in a very small village.
    I could see that statistic effect very clearly when i moved, or when i dated straight. It was like a different planet when i moved to a big city with a huge queer community. I was dating and finding compatible friends a lot more immediately.
    If you know many compatible queer friends, chances are much higher that you meet a compatible partner through them. Straight people usually meet their partners through work or friends.
    So you have to be aware of that. More therapy will not change that.
    And this problem aggrevates over time, because by the late 20s, many people are married and off the market.
    I can only suggest that you tackle this head on, for example by getting involved socially a lot. If you already do that, maybe consider moving to a bigger city, or at least get involved in a social group in a bigger city. And with big i mean 1 + mio size.
    Back then we knew from experience that anything smaller is too small. And today, as visible queer communities have shrunken even in big cities, this is more true than ever.
    It might also help to specify what exactly was incompatable, or what you were missing.
    If it's more tiny things like brushing teeth too loud, than it's more a personal thing. But if it's something like: not enough/ similar interest in culture/politics/sports, just too different as a person etc, it might also have to do with the place where you live.

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