You Need Help: All I Want Is a Relationship But I Can’t Make it Past the First Date

Q:

I’ve been in the dating pool going on five years now (I’m 27), and apart from a few situationships that fizzled out and one romantic connection that lasted a few months until I got my heart broken when I asked the “what are we” question and she bailed, I can’t seem to ever get past the first date.

I must have been on over fifty dates at this point, and nothing to show for it. I know dating is a numbers game, but it’s starting to feel like I’m doing something wrong. I’m not the most physically touchy or attractive person, so most of these dates end in the person saying they had a great time but want to just hang out as friends (if they don’t ghost).

These dates usually are at a coffee shop where we can just talk and get to know each other, and if they go well we usually end up talking for hours. I’ve tried being more forward, but it just comes off as unnatural and makes me feel embarrassed.

Friends are great, but I want more than that! I feel like my only options are to accept being alone (I’m used to keeping myself company but I don’t want to be lonely anymore) or to find a hookup (something I don’t really want).

How do I somehow give off that I’m girlfriend material? I just want to be wanted back for a change.

A:

Okay, first of all, I definitely want you to work on the instinct you have throughout this letter to undercut and ridicule yourself. Saying things like you’re not the most attractive or that your attempts to be more forward come off as unnatural makes me think you’ve gotten in a bit of a habit of negative self talk, and I think it’ll be important to repair your relationship with yourself when seeking a relationship with someone else. But also, I get that these things feed in to each other! It’s possible you feel not the most attractive because of your dating history, but even acknowledging that and trying to work through it will be important to do.

I also think it’s fine that you’re not a physically touchy person and that you feel awkward trying to be forward. That’s okay! That isn’t always 100% necessarily to make a connection with someone else, especially if it’s not the way you typically show your desire or interest in someone. That said, there are other ways to signal romantic interest outside of physical touch. I’m wondering if it might be necessary to shake up your go-to date destination. A coffee shop is indeed good for getting to know someone, but it also can have a pretty platonic connotation for some folks. Now, I’m not saying you have to go to some dimly lit romantic wine bar by any means. But perhaps introducing some other activity-based dates, like a picnic in a park or a walk around a lake (I’m not sure where you live/if these are feasible options!) or something that feels a bit more intimate than a coffee shop date could better signal what it is you’re looking for.

On the note of changing up your go-to date location, I think if you’re feeling stuck then it could help to shake things up in ways that are completely within your control. Get a new date outfit. Wear something that feels truly like you and that you feel comfortable in. Come up with creative questions to ask someone on a date rather than the go-tos. This not only will make the date stand out for the other person but also maybe make you feel a little less like you’re going through the motions, which might provide some comfort and confidence on your end.

I don’t think you have to resolve to finding a hookup or to being alone if those aren’t what you want in life. I’m curious how you’re meeting people. If it’s on the apps, have you made it clear that you’re looking for a relationship? This helps draw in people who are looking for the same thing, and while that doesn’t make them automatically compatible with you in all ways, it at least screens for the shared intentions. If you are using the apps and it’s starting to feel repetitive or bad, maybe shake things up and try to meet people in other ways, through shared interests or at in-person social events. I’ve had friends who have used matchmaking services when online dating hasn’t worked out for them, but that can definitely be cost-prohibitive.

I’d love for you to think about the things you’d like to bring to a relationship. What kind of partner do you see yourself as? How do you love and care for others? Try writing some of these things down as a reminder to yourself that you are relationship material, because I’m sure that you are! It’s just easy to get stuck in a rut and easy to think there’s no one out there for you, especially when people keep hitting you with the let’s just be friends. To better give off good girlfriend material, try to answer the question for yourself: What WILL make you a good girlfriend? Find the things to love about yourself.

Dating is often a numbers game, and there aren’t shortcuts. Dating, more often than not, entails a tremendous amount of luck, because it’s relying not only on your desires but on the desires of someone else and those desires lining up at the right time in the right place, etc. It’s even harder for us queer folks since the world isn’t set up for us to meet and fall in love the way it is for straight people. I say this not to bum you out but to assure you there are so many others in your exact boat. In fact, if anyone is reading your letter and can relate, I encourage them to say so. It’s easy to feel your loneliest when you think you’re truly alone in this struggle. Wanting to be wanted is a common experience.

When I was dating during the time period you note in your letter (ages 22 to 27), I did technically have some relationships, but they were not healthy ones, and even within them I was not desired in the way I wished to be. I met my now-wife RIGHT before I turned 27, and there were so many impossible to determine variables that led to that chance meeting. I’m not saying you’re going to meet your wife this year, but I just share my experience to note that while I did have some relationships in my early twenties, it wasn’t until I was later in my twenties that I found the right and lasting fit, and while I don’t necessarily regret those earlier years of my life, I did experience a ton of loneliness even within relationships and sometimes wonder what it would have been like not to jump into one so quickly. I think the transitional time of your early twenties is difficult no matter where you’re at with dating. But also, I have friends who are struggling with dating and finding the relationships they want in their thirties, forties, and fifties. It’s an issue that spans ages.

I’m sorry you’re feeling lonely. I don’t really believe in the whole cliche advice that people sometimes give that you can only really find someone when you aren’t looking. Because that’s just another attempt at a shortcut or an attempt to simplify what is actually always really hard! You don’t have to stop going on first dates (unless it feels bad), but I think that while you continue to seek them out you should also seek out an improved relationship with yourself, understanding what it is you want from a relationship and want to bring to one. Give off that you’re girlfriend material by reminding yourself exactly what makes you girlfriend material and believing in it. Hell, put it in your dating profile if you’re using the apps! There’s nothing wrong with saying it out loud!


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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 810 articles for us.

9 Comments

  1. I’m curious to know if the letter writer has been really interested in any of their dates? Like as a specific person and not just as a potential partner who could be anyone?
    I went on a bajillion okcupid dates and there were several people I felt like I WANTED to like – like LW, I really really wanted a girlfriend! – so of course it ended up awkwardly fizzling out each time. Even if someone is interested in you, I think they can sense when you aren’t really interested in them personally.
    Then I went on a date that was different, it felt different and exciting and so natural and fun and I couldn’t wait to see her again, to the point where I wasn’t even thinking about if we were going to be girlfriends in the future, I just wanted to enjoy it.
    Now we’re married. And our first date was in a coffee shop. :)
    Anyway I hope LW knows that whether they really like and want to date someone is just as important as whether the other person likes and wants to date them back. Someday they will go on the date that feels different and changes everything!

    • Your comment and the OP really resonated with me, I also went on a bajillion OkCupid dates that did feel a bit like repeating the same conversations, I’d often pick the same pub as it was comfortable etc, and also felt a bit awkward and not very forward. I wasn’t experienced and didn’t really know what to look for in someone beyond them being interested in me, and not “are we compatible? Can I grow with them?”. Before I met my first relationship at 24 (from a meetup group in the end) I think it was only with two women I went beyond two dates with, and again, I was more interested in them for the sake of wanting to be in a relationship than if we actually clicked. After COVID and my breakup I felt more confident going in with dating, had a better sense of who I was and what I wanted, looking for certain qualities and avoiding others, picking new date locations to mix it up and conversations started to feel different. I think it was my third first date when I was 30 I met my now girlfriend of nearly 3 years. Our first date was at a park and we pedalo-ed round the lake so it was very memorable.
      To OP – if your formula isn’t working, change something up. And be kind to yourself. Someone will appreciate you for who you are.

    • LW here, great points, thanks so much everyone for your thoughts!! It’s definitely something I’m working on – breaking out of that external pressure to “find someone” asap and instead focusing on what I actually want/need from a partner. I’m working with my therapist on building up my self-worth, and noticing what I have to offer outside of external validation. I’m really trying to expand my social circle this year and join new clubs to meet people organically – if anyone has any success stories of meeting people not on apps would love to hear!! Super resonate with mixing things up, dating has started to feel so stale when it should be fun!

  2. For what it’s worth, my preferred first date activity was trivia!
    – something to talk about when conversation gets slow but not so distracting that you can’t still get to know each other
    – a low stakes amount of pressure so you can see if they have massive anger/sour grapes issues
    – easy to leave when it’s done if you’re not feeling it (or relocate if you are, or stay if you are– many ways to play it)
    – you can get a sense of mutual interests and/or can find out if they’re too cool to care about anything (immediate dealbreaker for me personally)
    – usually not particularly expensive and sometimes there’s a fun prize

    Seconding the advice to be super upfront about looking for a relationship. People do get on tinder etc looking for friends so you have to be clear.

    Good luck!!! Dating can be such a nightmare!!

  3. I have pretty much been in one adult relationship ever (my current one) and I met my partner when I was 30! Sometimes it’s purely a matter of timing. Another thing to consider is who are you matching with on dating apps? Do you have a type (and if so, is that limiting who you meet up with)? Do you feel excited to meet these people? Like someone else said, if it’s someone right for you then you’ll feel that mutual spark. And you absolutely do not have to be physically affectionate to discover that! My first date with my partner was a social distance picnic in the park where we didn’t touch at all and it was still clear to me that we were into each other.

    I know it seems tough but hang in there! One thing that you have going for you is you know what it’s like to be by yourself and keep yourself company, so you don’t need to be in a relationship just to not be alone. That makes you a stronger person and the right person will love that you are CHOOSING them. Best of luck to you!

  4. I also think it’s important to note that two of the years when you were trying to date were pandemic years! Definitely not the easiest time to meet people. Lots of people are in the same boat :)

  5. I can definitely relate. I’ve been single for 12 years and haven’t met someone where there’s mutual interest in long-term committed relationship. Dating is hard! Queer dating can be harder! Also, who are these matchmakers these queer ladies are going to??

  6. I’m 25 and feel extremely similarly! Had a relationship in college with someone I truly did care for but it wasn’t meant to be and have been on and off of meeting up with people, situationships, and getting ghosted ever since. I decided to take some time (it’s been about 8 months at this point) to get back to a place where I liked myself and wasn’t going to let those things and the other inevitable pitfalls of dating tear down my confidence. I still haven’t found who I’m looking for but I know that it will work out in the end because I’m trying to prioritize me too! You got this!

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