Dear Roe,
I’m in my 30s, I’m a late bloomer, and I just really want to find love. I’ve tried putting myself out there. I’ve taken classes, gone to events and travelled a lot. I’ve used apps, but never matched with anyone I felt good about meeting in person. I’ve looked into matchmaking, speed-dating, getting set up, but nothing. I’ve also tried not trying (the whole “love will find you when you’re not looking” idea), but that has only ever left me stuck in the same place. I take care of my appearance, work on my self-confidence, pursue my interests, go to work, and try to be kind.
I want so badly to have a first date, a first kiss, a first love, and am finding it harder with every year that passes to stay hopeful. I know love isn’t something you can guarantee by following certain steps, but I’m lost and could use some advice.
I think that old “love will find you when you’re not looking” chestnut has long been misunderstood. Too many people hear it and assume they should stop being active in their pursuit of romance and let it find them, as if the perfect person will magically knock on their door one evening, interrupting Prime Time with this breaking news: I am your One True Love, I have been searching for you, and here I am!
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I don’t think that’s what it means, and it shouldn’t be what you’re banking on. When people talk about not looking for love, a more helpful interpretation is that when you’re not single-mindedly, laser-focused on finding lifelong love (but are still being active in your search), you’re more likely to find it. That’s because when people become laser-focused on love, when they begin to fear they’ll never find it and so become frantic in their search, when they cast lifelong love as the only thing that will make their life whole and worth living, when they spend years imagining the exact type of person that will fulfil all of their needs and make up for previous heartbreak or loneliness – all of that pressure becomes very limiting.
People discard others for not matching arbitrary checklists they think their perfect partner should have. They jump into first dates with the mode of an insurance evaluator, interrogating and observing for long-term compatibility instead of being present in the moment. The fear of more time passing makes them risk-averse, less likely to give people the patience, grace, and openness needed for some people’s wonderful specificity to reveal itself. The desire to settle down makes them rush through the early stages of getting to know someone, the unfolding intimacy, the connection building, as they instead dive into logistics and planning for the future.
I don’t mean to say that people shouldn’t be clear about what they want, and open about their desire for a long-term relationship. Particularly when people are in their 30s and if they want children, it of course makes sense to be clear in your intentions. But there’s a difference between approaching your love life with a long-term hope, and approaching people like they are candidates in a high-stakes selection process, where every interaction is quietly being scored for viability.
You are not behind, you are just at a particular point in your own timeline
The reason I’m lingering on this is not because I think you’re “doing it wrong”, but because I think the exhaustion and growing hopelessness you’re describing indicates that the way you’re approaching this is burning you out – and because burnout leads to resentment, cynicism, and a lack of openness, that’s not going to be sustainable. I’m also lingering on this idea because when you haven’t matched with one single person on the apps you felt comfortable meeting up with, I do suspect that the openness required to make a true connection with someone has been replaced with very exacting ideas about a potential match, and rigid standards that you’re using to dismiss people. I think you’re so focused on the long-term goal of true love that you’re trying to skip past the required early stages of dating – the clumsiness, the uncertainty, the awkward first dates, the giving that awkward first date a second chance because despite the awkwardness, they were kind and listened intently and maybe just need a minute to feel comfortable being themselves. You’re so desperate for love you’re trying to jump past the actual stages of falling into it.
I know you’ve put so much effort into your search, and I know the exhaustion that can come from feeling like you’ve done everything you were supposed to do and being frustrated that it still hasn’t worked. So we’re going to set aside the idea that you need to try harder or do more. When we do that, the question becomes less “What else should I do?” and more “How can I keep moving towards connection without this search hollowing me out?”
One way to think about this is to shift the goal slightly. Not away from love, but away from treating each step as if it must justify itself by leading to it. I would strongly encourage you to soften what counts as a “good enough” first meeting. Not in terms of your standards for how you’re treated, but in terms of initial spark. Some connections are immediate, but many aren’t. Giving yourself permission to meet someone who seems broadly kind and interesting, without needing to feel certainty right away, can widen the field just enough for something unexpected to take root. Remember that many people who struggle to put themselves across clearly on apps can come across quite differently in person, and when they’re given the time for their personalities to unfold.
Take the pressure off these initial encounters. When you meet someone in person, your initial encounter gives you a lot of information about their body language, how comfortable you feel around them, their cadence, the rhythm of the conversation between you. When you connect online or via an app, you get none of that information. So when you meet someone from an app for the first time, take the pressure off it being a First Date And Therefore A Very Big Deal. It’s not. You’re meeting someone to gather very basic information and see if you feel comfortable enough in their presence to arrange a second date. That’s all. For your dates, pick something that’s a nice experience in itself – a cafe you haven’t been to, a walk you enjoy, a spot beside somewhere you can explore on your own before or after - or ask your date to show you a part of the city they love. Make the dating itself a nice experience beyond its outcome.
Taking the pressure off makes dating more enjoyable overall and allows a connection to unfold more slowly and naturally, while also helping you temper your own instincts to judge and evaluate too quickly.
I do want to acknowledge that what you’re feeling is real, and difficult. It’s frustrating to feel ready for love and not to find it, and I think you’re also grappling with a type of anticipatory grief for experiences you haven’t yet had - firsts that feel like they belong to an earlier version of life. I get that. So many of our cultural scripts assume that everyone moves on the same timeline when it comes to romance and love, but let me tell you now that so many people exist outside of those timelines. You are not behind, you are just at a particular point in your own timeline.
Many people meet their first real partner later than expected, and when they do, the relationship is shaped not by what they “missed”, but by who they have become in the meantime. Good luck.
