Does Dating Work? 🤔

This issue is reproduced from my weekly digest on Revue.

I hope this doesn’t come across as bragging, but I have been on hundreds of dates in the last seven years. I occasionally marvel at my own stamina. If dating were a competitive sport, I would be under investigation for doping. If ‘putting myself out there’ was an Olympic event, I’d be on a Wheaties box. You get the idea.

It might be tempting to conclude there is something wrong with me. While that’s true, it isn’t the problem. I think the construct of dating is the problem. Or, is it what people bring to dating?

For the purposes of this essay I am defining dating as it exists for me: mostly online dating with some real-world dates.

Dating’s success rate in delivering relationships is dismal. Sure, there are people who meet online and fall in love, but successes are not the norm.

In my marathon-level years of dating I’ve noticed some prevailing themes that cause romances to derail:

  • Creating space. There needs to be room to enter another person’s life. Seems simple, but we engage in all sorts of activities and pursuits that keep others at bay, then are mystified when people cycle out.
  • The myth of the exceptional mate. The sooner we accept we are all flawed, in need of tolerance and patience, the sooner we can be generous with others.
  • Lost confidence. This is a big one in middle age. Divorces and setbacks undermine our courage. Instead of doing the internal work, we default to waiting for a person who is able to power through the gauntlet of gyrations we subject them to.

The problem with dating is that everyone is looking for lightning in a bottle amongst mere mortals. The illusion of choice make the stakes that much higher when we get face to face with another person. This person better blow me away!

“Someone I would be thrilled to do nothing with who would be as equally thrilled to do nothing with me.” Aziz Ansari

I’ve often thought this over-reliance on chemistry is partly caused by the romance fables we guzzle by the truckload. We inhale in all sorts of ways that love is a perfect person rather than what it actually is: a choice, generosity, forbearance.

Chemistry turns into a substitute for good judgment. We don’t have the slightest idea what makes a good mate or how to be one so instead we wait for unconscious signals and attraction to do the work of choosing.

‘Soulmates’ are exalted, while the couples who work at loving each other without the illusion of a perfect relationship are subjected to scorn. If we accept that the journey to love is an internal one and not on the back of another, then imperfect love seems the only realistic option.

The lasting impression dating has made on me is that we squander opportunity. We live under the delusion life goes on and on, and there is an unlimited supply of wonderful people who will come along. That we can wait indefinitely for that one, magic person to overwhelm all the barriers to intimacy.

It just isn’t so.



my two best pieces on dating ✍️

1*urll9dg7pzvnitzsagh5nw 2x

I Want a Sober Courtship
I couldn’t shake the feeling that the hot pursuit had little to do with how great I was and a lot to do with how this man pursued women. Go in hard and fast, get disillusioned with reality, struggle to keep up the momentum, withdraw, leave her bewildered.

Wash, rinse, repeat.

This piece is my biggest hit to date. It was shared all over Twitter and read several thousand times.

1*j scqbqlhsyne4s2kvidnw

Modern Dating is Inhumane
A tale of two men.

One was a hands-on Father of three, regular (but not sanctimonious) church-goer, owner of two sweet but smelly dogs, collected art, read the New York Times, and teared up at poignant, love songs. The other was a bright, swaggering executive seemingly pre-occupied with sexual conquest, and sporting a self-admitted vain streak. After an ardent romp, I made him talk to me (you know, like a hostage). We began a wonderful dialog that didn’t end until we parted.


20968887 111728282834912 634820596122779648 n

Alain de Botton, Always Wise



Get the Medium app

A button that says 'Download on the App Store', and if clicked it will lead you to the iOS App store
A button that says 'Get it on, Google Play', and if clicked it will lead you to the Google Play store
Rebecca Thomas

Rebecca Thomas


I build programs that produce lasting weight loss and lifelong well-being. My latest course simplifies real food cooking 🥑