You Need Help: Dating Makes Me Sad


I’m a queer cis woman in my late twenties and I feel completely undateable and with no idea how to get around it. When I try to put myself out there it typically has the effect of getting my hopes up and letting me down again, which leads to a few months of rocky mental health where I’m too afraid to try again. I can’t do this forever. I want to meet someone and at very least I’d like to have some kind of sex life, but every attempt seems like 1 step forward and 2 steps back.

I have lots of fantastic friends who are really supportive, but most are long-term coupled straight friends or queer friends who seem to find dating extremely easy, fun and plentiful, and neither group’s advice/ half hearted belief in my dateability really works for me. I have had two very short gay relationships that both ended making me feel worse about myself and dating in the long run. I hate clubs and bars, and every social attempt I’ve made to meet more queers has just made me feel like I’m not doing queerness enough/properly. I feel like I’m running out of ideas and am starting to feel the jealousy and difference from all my loved up/sexed up friends. How can I stop myself becoming a bitter single hag with dreams of queer love that are too painful to pursue?


I think the best thing you can do for your dating life right now is to actually take a break from dating.

I don’t buy into the idea that you can only find someone when you’re not looking for them. But I do buy into the idea that our bodies and minds are often trying to tell us things and it’s hard to listen. It really does sound to me like dating has put you in a bad place mentally. Dating is hard, and it’s fine for it to feel hard! But it shouldn’t lead to this much mental unrest. If every time you jump into dating it leads to rocky mental health, then I think taking a very intentional and productive break might be what’s best for you right now.

Now, you may be wondering how that differs from other breaks you’ve taken from dating as you imply in your letter that you intermittently put yourself out there, hit that bad mental place, and then stop before putting yourself back out there again. But I think deciding to take a break before getting to that point of rocky mental health that forces you to take a break will make a difference. And the words “intentional” and “productive” are important here, too. The break should feel like it’s on your terms and it should also be a time where you actively work through the feelings that make dating hard.

You are not undateable. I promise. But feeling jealous of friends and also like you’re not “doing queerness” properly are deep-rooted insecurities that are likely holding you back from living your best dating life. I sense an internalized fear that you’re not “queer enough,” and let’s just toss that out the window, okay! You’re queer enough, and there isn’t a “right” way to be queer. If queer bars and clubs are uncomfortable for you, then don’t force yourself to go to them. There are other places and ways to meet queer people, I promise. But also, that’s not what we’re doing right now. We’re focusing on you and on addressing these underlying insecurities.

I feel like it’s common for people to talk about the societal pressure placed on straight women to find a lifelong partner, get married, etc all before the age of 30, but I think there’s often just as much pressure on queer women — plus some additional pressure that feels unique to our community. I don’t know everything about your life, but I do know it can be hard to be queer. Having a partner can feel like a lifeline for queer folks who have complicated relationships with their families or otherwise face social hardships in life. Queer love seems like the obvious antidote to queer suffering. On top of that, I know a lot of people feel like their queerness is somehow inferior or needs to be “proven” to others when they don’t have a partner. But I think all these pressures are bullshit! 1. You can find queer love outside of a romantic relationship and 2. Your queerness is valid and complete whether you’re single, dating, in a long-term relationship, married, etc.

But I also hear you. You want a relationship. Or at least you want to meet someone you have a connection with and also have some sort of sex life. You’re not asking me to present an alternative to any of that. And I promise I’m not! I’m just asking if you’re actually getting anything out of forcing yourself to date right now. I’m just asking if you might have a better shot at dating in the future if you focus intently on yourself and on unlearning the roots of your insecurities and fears. And I’m also telling you firmly that late twenties is not too old. As queer people, we can sometimes feel like we’re somehow “behind” our queer peers, but that feeling is definitely rooted in broader societal pressures and expectations.

It makes a lot of sense to me that you’re especially feeling this way after damage done by two relationships that didn’t pan out. It might help to do some reflective journaling on those relationships. But then feel free to relegate them to the past. Those two relationships do not define you, and they do not doom your future dating prospects. Even though you say they were short, it’s possible you haven’t taken enough time to heal from them.

You won’t become a bitter single hag. I’m bolding these affirmations in the hopes you’re able to really ingest them. Vanessa’s self-work homework assignment to assume everyone thinks you’re hot and desirable remains forever useful. Start small with your self-work: Make a list of the best things about yourself. Start with five things. Then do ten. Then do 15. It will feel hard, and it will feel awkward. But the things you love about yourself are the things someone else can love, too.

I hope you have friends who let you complain to them. I hope you don’t feel like a burden when you do. Dating is hard, and I feel like it’s important to talk about it being hard. You’re allowed to complain about it, to commiserate. Because that’s the other thing: You’re not alone in this feeling. You’re not the only person who thinks this is hard, who gets stressed or sad during the process of going on dates and trying to meet people. After you’ve taken some time to really focus on yourself, I encourage you to think of any of the parts of dating you do like. How can you approach dating in a way that feels the most comfortable to you? I have a friend who hated apps, hated going out due to her super busy work schedule, but still wanted to meet someone and deeply connect. She ended up using a matchmaking service, which costs money and therefore isn’t an option for everyone, but I’m just sharing because she basically had to slow down, step back, and think outside the box about how to make dating work for her. I think there could be other options out there for you, too. But first I think you need to step away from dating before you can figure out how to crush it.

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

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Kayla Kumari Upadhyaya

Kayla Kumari Upadhyaya is the managing editor of Autostraddle and a lesbian writer of essays, short stories, and pop culture criticism living in Orlando. She is the assistant managing editor of TriQuarterly, and her short stories appear or are forthcoming in McSweeney's Quarterly Concern, Joyland, Catapult, The Offing, and more. Some of her pop culture writing can be found at The A.V. Club, Vulture, The Cut, and others. You can follow her on Twitter or Instagram and learn more about her work on her website.

Kayla has written 839 articles for us.


  1. being single in yr 40s sucks. i’ll be turning 40 in a few days and already i feel much older than most queers around me. i don’t mind dating ppl younger than me if we click, but most of the time i feel weird and predatory about it, and anyway i do prefer to date ppl my age or slightly younger as i find i have more in common w/ ppl in my age group but most ppl in my age group are already coupled up. i don’t rly know how to change this esp as i’ve pretty much cut almost all use of social media. online dating has been pretty terrible. i do go out, i do organizing work in my community when i have the opportunities to, but despite all that, here i am still single. anyways i can only hope that my luck will change in the new year.

    • My experience (and that of several other queers I know well) is that dating in your forties is fantastic! Both I and the people I went out with were mature enough to know ourselves and our baggage, experienced enough to communicate effectively, and motivated enough to make change and adapt from a place of strength when it came to building a relationship.

      What absolutely sucked was being about to turn 40 and making it a big deal in my head and telling myself things that sound a lot like this comment. I didn’t believe an older friend when they told me dating in your 40s was great, but it turned out to be true.

      I truly hope you have the same experience, because if so, you have a lot of fun ahead!

  2. Thank you for this, I just turned 30 and am in a very similar situation. All of my straight friends are married and most of my queer friends are at least in solid relationships, and I do feel behind and like I missed my chance, and like the letter writer am dealing with deep insecurities. I appreciate this response!

  3. Feeling chronically single after 25 is a bummer. It took me 4 years to find a good partner after I got out of a relationship at 29. In my eyes everyone could find someone except for me, and it was hard since I kept comparing myself to other people. It was hard to see others who were hot messes find someone and get married when I “did everything right” and was alone. I did go out a lot, and implemented rules to make the rejection easier.
    I won’t lie and tell you I stopped comparing myself to other people, since I didn’t. Therapy helped, distracting myself with other things helped. I got really into my career, helping my family and friends, and connecting with my values, which were ultimately all the things that my partner admired about me from the get-go.
    TL;DR: Swipe a lot, but have hobbies and other things that make you happy. Also I love the Matchmaker Maria. She is mostly for straight people, but I found some of the stuff was pretty helpful.

  4. This question could’ve been scooped directly out of my subconscious. I’m 33 and I’ve been on every dating site and app since I was 19. It’s never really worked out for me, I’ve been on a lot of awkward dates and gotten my hopes up over and over. I’ve just never found that connection. It is really hard seeing everyone else around you find love and not being able to find it for yourself. The “oh you have love from friends/family/etc” sentiment just presses on the bruise. I am loved, but even my deepest friendships don’t fill that void of wanting to share my life with someone in a romantic sense. I’m confident and I have a lot to offer, but finding your person is largely a roll of the dice. I’ve done apps, personals, Craigslist, trying to meet people through friends, going out, going to queer events, putting lgbt stuff in my work station, Instagram, making friends through fb groups etc. I’ve done everything you’re supposed to do and it’s just never worked out. All I can do is have a good cry about it when it gets too painful and keep trying. Maybe it’ll work out eventually. But I kind of feel the same way about the lottery. Some people get lucky and some don’t. The one thing that keeps me from absolute despair is reading fanfiction. Living vicariously through the characters finding love soothes that hurt a bit. I highly recommend it, for all us unlucky folks.

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