I am about to be 38, feel like I have lost timing for a relationship.
I have a really good friend who is around my age. I remember when we both got divorced in our mid-20s. We both had sons, but other than that, we didn’t have much. We were barely making ends meet: he moved back in with his mother and didn’t have a car and I was living in a deteriorating, lower-class apartment, had a very simple and functional car, and barely 10k in the bank.
Even during that time, though, there was always hope. I remember at one point I was dating multiple women I had met on tinder as I had no social circle where I was at. I had been working out a lot, was in amazing shape, dieting religiously, and felt confident, which seemed easy as going to the gym given my circumstances felt like an upgrade compared to staying home.
We were both dating at a relatively high level, but he chose a woman who wanted to grow together, build a family, and settle down. I, on the other hand, was always chasing the hotter, more beautiful women. Since I don’t consider myself good-looking (my confidence came mostly from being in great shape), that often led to toxic relationships, filled with anxiety and feelings of abandonment.
Now, at almost 38, I feel like I’ve lost my timing. After more than 60 tinder dates over the past 6 years and multiple cities, the women I meet my age, I often don’t find attractive or exciting, or engaging. They are either super fit and gorgeous (which is like 1 out of those) and and don’t seem interested in me at all or just ghost me or they are boring and feel like a project. I’ve spent years getting frustrated with dating apps and meeting people in person—situations that feel like blind dates, even after weeks of talking.
I have a very good job, a salary that would be considered “rich,” but I’m getting burned out. In my field, I need multiple contracts, and after five years of intense effort, I feel exhausted. It feels like time is running out. In my 20s, everything seemed possible with just energy and a good body. Now, in my late 30s, I have a house, a good car, and a high income, but it just doesn’t feel doable anymore.
I no longer get confidence from my looks, and honestly, I don’t look as good anymore. I’ve gained weight. Even though I earn well, I don’t feel rich because I need to plan for the future and make sure my son’s needs are met and secure. Sometimes I feel tempted to buy a crazy car or rent an amazing apartment—but why? I had the body before and it didn’t lead anywhere meaningful. I have the money now, and it hasn’t changed much either. I don’t want to trap myself financially, especially when I already feel burned out.
I’ve tried countless activities—CrossFit, dance, yoga, and more. I always try to be friendly, smile, break the ice, start conversations, and follow up. But nothing really leads anywhere. It feels forced, like trying to build a friendship during an elevator ride when the other person just wants to get to their floor. Nothing flows naturally.
I’ve tried meetup groups. They can be enjoyable, but it’s hard to connect deeply since everyone is at such different stages in life. Sometimes you’re talking to a grandmother, other times to a student—it just doesn’t click. The reality is that after putting in so much effort, I feel like I have nothing to show for it: no close friends, no meaningful relationship, no fulfilling lifestyle.
I’ve even tried dating women I don’t find particularly attractive but who I know would make good partners. But I end up preferring to be alone—it feels like a chore. At the same time, I feel deeply lonely. I work from home. I’ve been in therapy for years. I could probably get a PhD in self-help and mindfulness. I’ve tried psychedelics, everything. And still, I feel stuck with this void.
It’s a void that seems to get filled when I’m excited about a relationship or when I have a close friend—neither of which I currently have or seem able to find.
So I’ve been coming to the conclusion that my time has passed. The time to build lasting friendships was in college—but I studied in another country, and those friendships didn’t carry over. The time to meet an attractive partner was in my 20s, when I was fitter, better-looking, and had more freedom. That time feels gone. Now it feels like I’d need to get back into great shape—which I don’t have the energy for—or buy an impressive car and keep pushing myself even harder. But neither of those things has led to meaningful relationships for me before, so why keep trying and risk wasting more years?
I feel like giving up and just going off to explore—travel, live in nature, maybe move to a small town. But I know this need to connect, to feel chosen, to belong won’t go away, it might actually intensify.
I’ve traveled alone and stayed in top hotels, and it felt miserable because I had no one to share it with and it just feels better to be lonely in my own apartment rather than in an expensive hotel room I don't want to be in. When I stay in hostels, I feel better because I can connect and interact. Still, I don’t want to live for fleeting connections and drunken adventures—especially at my age.
Just needed to vent.