I haven’t made it past a first date in months

‘Over time I’ve started to imagine myself as the Coyote, continually chasing the Road Runner’

Love Letters

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Q. I’m a straight man, employed, love dogs, bearded, a foodie, a nerd, and live a fairly active lifestyle. I’m relatively new to dating. I’m also sick of dating.

I made it to my 30s without ever having been on a real date, and I truly didn’t feel like I was missing anything. Then, when I noticed the first couple of gray hairs appearing (two quickly became four, then more than I could reasonably pluck out and not have a bald spot), I started asking myself some more existential questions. Around the same time, COVID started, and I was isolated from most of my friends/support group for a while and I finally realized what my problem was: I was lonely. And almost overnight, it became a powerful, immutable, devastating loneliness. So I decided to make a major change in my life. A dating app! Should be an easy fix, I thought. Besides, I don’t drink, and I wouldn’t be caught dead dancing, so meeting people at bars or parties doesn’t really work. I’ve never been the type to approach a woman in public, out of the blue (where does that kind of confidence even come from?), so I appreciate that the app lets me find people who, supposedly, want to be found.

But over time I’ve started to imagine myself as the Coyote, continually chasing the Road Runner, and every scheme ends with me falling off a cliff, crushed by a boulder, etc. Tons of women like my profile, which is a nice (much needed) confidence boost. I’ve had hundreds of total matches, but almost none of the profiles I like get a response. The conversations I start rarely turn into dates, and inevitably end with me being ghosted. Or a few times, I have come to realize the only thing keeping us going was me. Isn’t this 2022? Do women still largely want to be chased, expecting men to show all the initiative? Or is that just the women I attract?

More importantly, I’ve recognized a cycle repeating itself. Excitement to match with someone pretty/fun/interesting, followed by one to three awkward dates, and eventually despair when they move on, with or without a goodbye. The handful of times I’ve managed to string a few dates together with someone special, I’ve failed to initiate intimacy, and I suspect this is my biggest flaw. During the almost two years of this, there was one girl who stuck with me for two months. She was great, but we never moved past kissing, and eventually I had to admit it was because I wasn’t physically attracted to her.

Lately I’ve noticed a regression — my conversations end faster, even fewer of them turn into dates, and I haven’t gotten past a first date in months. I guess this is dating fatigue, but it just feels like apathy. I dove into this headfirst, assuming I’d need all the practice I could get, but I have nothing to show for it. Now I’m not sure what the next move is.

HARDHEADIPUS OEDIPUS

A. I had to Google your name to get the Oedipus story out of my brain. Readers, he’s making a Road Runner cartoon joke. Moving on.

A lot of people in my life believe in energy. Vibes. Whatever you want to call the noticeable feeling we bring into a room (even a virtual one). Right now, you seem to be radiating energy that screams, “I’m finally ready! Let’s do this! Please!” I don’t know if that’s what’s pushing people away, but it could be. I’m not blaming you, to be clear. These women are ghosting, flaking, and not doing much to maintain momentum. But a lot of dating is like being in a maze, turning in another direction after you hit a wall. You have to be ready for a lot of false starts. You have to go in thinking, “No wild excitement until we see what happens.” You don’t have to be aloof, but calm is nice.

Let’s not make any generalizations about what women want or do on apps. Everyone is a different human, and in 2022, people are overwhelmed, busy, and dealing with their own dating fatigue. If it feels like a chase, let it go.

If you’re feeling apathy, limit yourself to a small amount of time on those apps. Maybe 20 minutes a night and then you’re done. Message someone a few times and move to text if it’s worth it. You don’t need to be staring at faces for an hour.

Also, when it comes to the intimacy thing, sometimes the way to get over this is to say what you’re thinking. As in, “I’m wondering about kissing you. I’d like to. Thoughts?” Readers will probably have a smoother line. The point is, sometimes talking about kissing (and other things) makes people think about kissing, and it also gives the other person the chance to say, “Yeah, do that!” That can make the whole experience less intimidating.

This is a journey. You’re on it. Take breaks when you need to, and be patient. Also, stay as close to your support system as possible, even virtually. That helps.

MEREDITH

READERS RESPOND:

You mention dogs. Do you have one? I adopted one during the shutdown and I’d no clue how it would change things socially. I met people out on our walks, through local dog groups on social media, etc. I’ve lived in my town for years but it wasn’t until I got my dog that I felt like I found a community. Having a dog is an instant icebreaker — and I sense it would make you feel more at ease too, rather than relying on dating apps.

DANGLEPARTICIPLE

“I wouldn’t be caught dead dancing” Why is that, sir? Are you under the impression that something bad happens when you take a woman into your arms? My wife and I took up ballroom and swing 10 years ago, and my, do we wish we’d done so much earlier.

RETSMAHX

Many folks don’t even get to first dates, so you’re doing something right. Dating can be a slow and tedious process, especially if you are focused on the end goal. Plus, you got a late start. Don’t try and cram a lifetime of dating into one year. It takes time to weed out what you think you want from what you really want.

WIZEN

Send your own relationship and dating questions to [e-mail]. Catch new episodes of Meredith Goldstein’s “Love Letters” podcast at loveletters.show or wherever you listen to podcasts. Column and comments are edited and reprinted from boston.com/loveletters.