‘I’m a Thirty-Something Lesbian Worried I’ll Be Single Forever’

Q:

I’m a lesbian in my 30s who has been single for 5 years and not for lack of trying. And I mean that. I’ve gone on dozens of first dates through dating apps, I’ve collected many random hobbies over the years by taking classes to meet people, I attend things on my own all the time, and even recently I tried speed dating for the first time. Still, I haven’t had even the glimmer of a relationship. Haven’t even so much as kissed someone in a few years.

And I’m a total catch! I have a great job, I own my house, I’m smart, cute, and don’t speak to any of my exes! I even live in an area that is relatively queer. Yet, I’m starting to become convinced that it’ll never happen for me.

In some ways it feels like I’m waiting for the next part of my life to begin with a partner. I bought a house last year after putting it off because I had been waiting for someone to do it with and realized that I may be waiting forever. But it was an incredibly lonely experience. And I’ve had so many experiences over the last few years that I always pictured myself sharing with a partner.

If I had been sitting on my couch for the last 5 years without trying, I would understand. It’s much more painful to feel like I’ve been doing all the “right” things to try to meet someone and still come up short. Everyone in my life says I’m wonderful and to “put myself out there” but that doesn’t seem to matter. And as time passes, it becomes more difficult to hold onto the belief that I am worthy of love and will find it.

I guess my questions are: Where do I go from here? How do I keep trying without losing hope? Should I be doing anything differently?

A:

This is the thing that is most frustrating about dating imo! You can literally have everything going for you and also be truly putting yourself out there, and you can still struggle to find someone to actually date. It sucks! I have many friends spanning ages, locations, and sexualities for whom this exact situation you’ve described is true. You’re single, but you’re not alone. I believe you when you say you’re a catch! Being a homeowner ALONE should qualify you for a long line of prospective girlfriends. Owning a home?! In THIS economy?!?!! I’m impressed!

While your friends’ advice to put yourself out there is coming from a good place and indeed is the most common response to folks feeling like they’re stuck in singlehood, clearly you already are putting yourself very out there. I’m left wondering if you’re almost putting yourself too out there, casting too wide of net. That’s not a criticism! But I’m trying to figure out something else you could try so as to at least not feel like you’re in a slump. What are you looking for in a partner? What are your priorities in a relationship? Write these things down. Maybe instead of going on dozens of first dates via the dating apps, get a little more intentional with who you’re planning dates with and seek out people who fit certain things you’re looking for. I know this is sort of contrary to conventional How To Date advice, but I think it could accomplish a few things here.

For starters, the sheer volume of first dates you’re going on and attempts to date you’re making may be contributing to your feelings of exhaustion and the pain of continually putting yourself out there to no avail. It’s possible you have feelings of dating fatigue! That would be understandable! It could be better for your overall mental state to scale back some of your dating efforts while still managing to put yourself out there to some degree, which could set you up for long-term success with dating. It also could mean more of an emphasis on dating people you have some baseline compatibility with. Getting intentional about your priorities in a potential partnership can teach you a lot about what you’re looking for and then set you up to go out and find what you’re looking for!

But of course, it also isn’t as simple as just that. It takes time, but the thing we talk about less is that it takes luck. Especially when we’re queer, our dating pools are just naturally smaller. Even in a big city with a lot of queer people. You are worth of love, and I think you will find it. There is always time, and it’s never too late. If you’re low on hope, borrow some from me! I do have hope for you! I have hope for everyone when it comes to finding love, truly.


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, 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 A.V. 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 1050 articles for us.

14 Comments

  1. Dear letter writer,
    I, too, know many people who are in a similar situation to you (but without the house:). Surely, this does not change that you feel something you wish for is missing from your life, but I want to second Kayla in two things: a) you are not alone, and b) there is so much luck (or the lack thereof) involved in dating.
    You asked if you could do something different. I just want to point out that you are doing a lot of work already, and sometimes, that only means that the discard pile gets really big.
    I have a few questions that might be paradoxical:
    → What if there is nothing to fix? What if you already do (or did) everything you could, and there is no need for self-improvement? What if you say to yourself: I am trying, and I know want something different for myself, but I also know the result is not in my hands and I cannot control the outcome? (It might make it easier to exhale because what you describe gives me an impression of breathlessness.)
    → Why are you trying to date? (That is not a judgment or a criticism. Nothing wrong about wanting to be in a relationship!) Maybe you can dive into what you would like from a relationship (if you haven’t already). What exactly do you miss? What exactly would you like to be different? Is there anything that people in your life at this point can provide that you would like to see from a romantic partner? Surely they cannot replace what you want, and it does not minimize this feeling of loss for you. Sometimes people feel like “If I don’t have this, I don’t have anything!” – and there is so much space between these scales.
    → What if you gave yourself a break? What you currently do sounds like a lot of pressure and as if you did everything to ace the test (of dating). What if you stopped for a while and see what’s that like for you? As an experiment. No good, no bad. I tried dating, and it made me feel______. I tried to take a beak from dating, and it made me feel______.
    → How can you take good care for yourself in the time you don’t have what you long for? How can you show up for yourself and meet your own needs as much as possible while recognizing that you would like a different life for yourself?
    Maybe you’re doing all of these things (and more) already. In that case, ignore everything that does not fit!

    If you are interested and you haven’t read these articles yet, I can highly recommend them:
    https://www.autostraddle.com/i-am-single-and-my-life-feels-meaningless/
    https://www.autostraddle.com/how-do-i-date-when-im-attracted-to-hardly-anyone/

    • This reads nearly verbatim to therapy advice I have received in the past.
      100% applicable and helpful for LGBTQIA+ folk with low to mild level mental health complications.

      Unfortunately CBT can only go so far and help a certain subset of individuals.
      Apologies to my former counselor Rebecca, for being a CBT resistant terror.

      I will be forever cross with Rebecca and her coworkers for ‘hiring’ me a few years later, just to surveil me and observe my behaviors. Like an animal in a zoo. I do believe this is a violation of social work ethics. Especially if information was passed along to outside parties. Sounds like breaking HIPPA and Social Work Ethical Code.

      On the off chance this is indeed the same Rebecca, I’m glad you can help some people. But when CBT is your specialty and that specialty isn’t working, do refer out. And for the love of god do not go along with hiring someone to surveil them. It might be a good time to review the Social Work Code of Ethics.

      https://www.socialworkers.org/About/Ethics/Code-of-Ethics/Code-of-Ethics-English

    • Hi, I am really sorry this happened to you! What a shitty thing to go through! I am actually a very different Rebecca – just a stranger on the internet who apparently said something similar, who isn’t trained in psychology and just had some thoughts to share.
      All the best to you!

  2. I have complicated feelings about telling someone that they will find a relationship. I know – the intention is very sweet & kind! However, we cannot “promise” someone something when in fact no one knows how other people’s futures will look like.
    To clarify, I don’t mean to attack anyone here. Receiving the message “you’ll find someone, it’ll happen for you one day, too” might be exactly be the letter writer loves to see/needs to hear! People are so different! Personally, I don’t feel good when someone tells me this. I spend a lot of time with grief activism. In grief, people are quick to point out to a grieving person that things will get better. And that is very possible. But they don’t know; things can become worse as well.
    Grief is not only a thing when it comes to death, but also when life doesn’t turn out the way we had hoped (ambiguous loss). From what I’ve seen so far, saying “it will be better/ you’ll find someone…” often takes place when it’s hard to hold space for someone’s despair / sadness / uncertainty. What I personally have found helpful is something like: whatever happens, I hope you can trust yourself to take care of yourself and that you have people in your life who support you. And: I hope you can live this in a way that feels true to yourself and that you can be proud of yourself, given this is the life you have now though you wanted differently.

  3. Isn’t there space for both Ellybelly and Yasmine’s sentiments?

    Ellybelly’s message seems to be one of hope. Although the message could have been more explicitly named hope, shouldn’t there be room for this? In context of online messages on forums, I think this type of message has a place without being dismissive. Having hope is not inherently a bad message.
    Living with or being close to and in contact with someone who couldn’t figure out how to ‘hold’ grief of, or be present with, a grieving person is a different story. That could ‘make the grief worse.’ I’m don’t think this incident is that situation, but it’s good to be aware of. Toxic positivity won’t lift the grief off a heavy grieving heart.

    Yasmine’s message is more focused on attention on what can be controlled, like building self-confidence, and creating a supportive community of likeminded people who share goals. Note the attention shift from the grief to action while simultaneously gently reminding those who are grieving that it’s okay to feel the grief, and that there is more immediate hope in other areas of their lives. Reviving agency is key, and I think it is a fantastic message of hope with some general direction for action.

    (I assume) We all know that life is a series of ups and downs. Things get better and worse all the time both in small everyday ways, and in chapters of years being ‘better or worse’ than the last. This is all in flux.
    Because that’s a given, I really do not think it’s helpful or worthwhile to use the framework of “you don’t know (the grief) it’ll get better- it could get worse.”
    Unless something seriously out of the norm happens, life kind of will drudge on like business as usual, with small moments of contentment, joy, inconvenience, anger, ect.
    Ideally, with the agency of the griever, the situation will improve due to their own efforts.
    That’s the hope at work.

    It is true, people today generally do struggle to know how to be present with someone who grieves and sometimes can do more harm than good in these interactions.
    At the end of the day, a message of hope seems essential. There are different ways to offer the message. Ellybelly’s message comes across as a more casual message of hope and validation (the ‘been there too, it’s real’ kind). This approach does well with general everyday encounters/interactions.
    Yasmine’s message offers the sit with you in the feelings validation plus attention shift to areas with more personal agency. Generally, I’d expect this with a small handful of people in life, or my therapist.
    It’s a wonderful approach, but should be used with discretion.
    Using Yasmine’s approach with everyone who grieves is almost certain to create emotional burnout. And perhaps the resentment that comes with it. Again, great approach, use at your own discretion.

    Anyways just the two cents from someone with too much time on a hot summer day.

    • I get that many people want hope. Hope can be wonderful. To me personally, hope is a big vague concept that can mean so much different things. When hope is mentioned generally, my question is: hope in what? Hope in whom? Hope in how?

      For example, if I hope that I will be in a wonderful relationship & have a good job in one year, that’s hope in a very specific outcome, and if this doesn’t happen, I will likely be disappointed & feel bad. I may consider myself a failure because it did not turn out the way I wanted, and I may think that I didn’t do my work “correctly.” But if I say to myself: how do I want to feel in the next year?, that feels different. Then, I can ask myself: what can I do / what is in my power to make it more likely that I will feel this way?

      Hope in something very specific (a speedy recovery, getting pregnant, someone waking up from a coma…) gets disappointed all the time. So my approach now is: how can I take care for myself and how can I carry myself through this – given that this is what I have to live?

      I agree with you that life is a series of ups & downs and things get better & worse in small & bigger ways. And then, there are a number of people who had major successive losses in a short time period. If someone tells them: “In five years, it can be much better!” they are like: “Well, it can also be worse. Five years ago, I had no idea that my mom would be murdered, my ex-partner would not survive their car accident, my friend would die of cancer and I would miscarry. So I am dreading the years to come.”
      That might not be the norm, but I cannot tell you how many people experience a number of deaths or other devastating and life-changing losses in a short period of time & consequently expect bad things to come their way precisely because this was their experience.

      You said that using my approach with everyone who grieves will almost certain to create emotional burnout. Can you say more about it? Personally, I have made better experiences with it than with casual hope/encouragement I used in the past because people felt I didn’t understand them/ their grief / pain / whatever the case. But I would like to hear more.

      • Sorry to hear about the unfortunate series of losses, ie: death of mother, partner, friend and miscarriage. That’s tough to hear.

        Grief work is incredibly emotionally exhausting. You don’t have to be a nurse or therapist to experience it. Although those professions will have high levels of exposure at the workplace, family members, partners, friends, or anyone emotionally close to someone who grieves has a higher risk level. Same goes for those with generally high levels of empathy.
        Our society isn’t really structured in a way to properly support many individuals, including those who are grieving, or those who care for the suffering.

        Hopefully this article can explain both burnout and compassion fatigue better than I can.

        https://www.verywellmind.com/compassion-fatigue-the-toll-of-caring-too-much-7377301

  4. I feel you, letter writer. Also, I love the thoughtfulness in the response and all of the comments.

    I have had a few relationships over the years with increasingly longer periods of being single. I have built a beautiful life with friends and community during my time as a single person, but I still deeply yearn for a romantic relationship. Sometimes I get frustrated with myself when I think about how it is that the one thing I want above all else is not attainable right now and the love for my amazing friends just doesn’t fully fill that void.

    Recently I spoke with my therapist about how to move forward in life and do things I always planned to do with a partner, like maybe buying a condo. It’s been a heartbreaking process in many ways but I just have to hold on to hope that I will find my person and they will fit into the life I have built and I into theirs. For me, this hope is what keeps me going. Some days the 30 somethings dating pool feels extra small, but I try to remind myself that people move, break up, come out, etc. every day and I do believe one day I will find my person.

  5. I was single for many years and what helped me was understanding that there is literally nothing wrong with me for not finding a partner.

    After a long break from dating, once I put myself back out there I was encouraged to pay attention to how I’m feeling during the date and be open to any outcome; rather than wait for the dating to “work” and result in a relationship.

  6. I’m mid 30s and have made peace with never finding a romantic partner. It is what it is. I find it easier to plan my life around never being in a romantic relationship than hoping it will happen one day.
    Very few people fit my standards and I refuse to budge on them, even if it means never dating again.

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