Dating is draining

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If you want an activity tonight, I'm moderating the Harvard Book Store Zoom launch of this very funny memoir, and it's very Love Letters-ish, and the author has been on the podcast. You can sign up with the link. There will be visuals.

My story: I’m 49, male, very successful in my career, and I have had very little relationship experience and no long-term relationships. I've had four shorter ones, none lasting more than four months. I have struggled with depression and low self-esteem my entire adult life; it held me back for many years. For long periods I put no effort into meeting women and focused on my career instead. I’m also introverted and have always had trouble meeting people.

I finally started therapy about five years ago and it has been helpful (I've also tried several depression medications without much effect), but not a cure. Therapy helped me put more effort into dating in the past few years than I ever had before. But it has been very frustrating. Over the past eight months I met three great women who I thought could all be matches; I dated two briefly, but they both ended it for what I considered to be irrational reasons. The third ended it after a few dates because she had a son and I don’t have children, so she felt I wouldn’t be able to "relate" to her. After these disappointments, I now want to stop making deliberate efforts to meet women, as it’s mentally draining.

So, absent having a loving relationship just happen organically, I'm potentially facing a life without ever having been loved. It feels very daunting to accept this. Any ideas?

– Gloomy Gus


First, there are a lot of people with years of relationship experience who feel like they've never been loved, at least not properly. Please don't assume that everyone else comes to the table with more (experience, confidence, happiness, etc).

Second, this phrase stuck with me: "it's mentally draining."

When I read those words I thought, well, welcome to dating. There's a reason I made "dating fatigue" a category for our letters. Mainly it's because pre-pandemic, at least, a lot of people were very tired of constantly swiping on apps, having meetups, and never quite finding the match they hoped for. Some of those people now long to date because they've been isolated for so long.

Anyway, my point is that if you've had several "almosts" in a row, if you've made it to third and forth dates, you are doing the thing that gets you to finding/being loved. My advice is to avoid making big rules about what you will and won't do. You need a break from "deliberate attempts" for now, so yes, avoid apps (if that’s how you were finding people), but please don’t say "never." You might want to try again, whenever it’s safe. You're allowed to change your mind.

There are no absolutes here. Don't accept that narrative that you'll never be loved. It's one possibility, but there are so many other ways this could go. Work with your therapist to come up with visions of success in love. Learn to tell yourself a different story. Also talk about what it would feel like to be in love, as opposed to being loved. That's just as important.

– Meredith

Readers? When you get into a "it'll never work out for me" moment, how do you get yourself out of it?