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!

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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.

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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.


You can chime in with your advice in the comments and submit your own questions any time.