8 Harsh Truths About Dating (from a former professional dater) – Love Your Work, Episode 258

June 24 2021 – 07:30am

8 harsh dating truths I once was a professional dater. I was good at getting dates. I was terrible at finding a partner – which I really wanted. I went on so many dates, I made $150,000 on an online-dating-advice blog (which I recently shut down).

Listen to the Podcast

Listen in iTunes >>
Download as an MP3 by right-clicking here and choosing “save as.”
RSS feed for Love Your Work

I’ve now been in a relationship for several years. Here are the harsh truths I wish my single self had known.

WANT TO WRITE A BOOK?
Download your FREE copy of How to Write a Book »
(for a limited time)

Dating is noise. There’s nothing about dating that has anything to do with being in a relationship. Dating provides false signals. If someone is exciting on a date, that’s often a sign they’ll be a nightmare in a relationship. If someone is boring on a date, they may be great in a relationship. I don’t know how to fix that, other than be very careful how you judge whether or not a date went well.
You’ll never be “ready” for a relationship. Self-help books will tell you, “You have to love yourself before you can love someone else,” as if you’ll never be ready until you’ve achieved the platonic ideal of a fully-formed human. At that point, you and another fully-formed human will fit together like puzzle pieces – forever. More likely you’ll meet someone who’s screwed up in the perfect way to complement your own screwed-up-ness. You’ll change one another, and your best hope is the people you change into will also be compatible. You’ll never be “ready.” You’ll always be changing.
Yes, you need someone. Once in a while you might decide you’re fine being alone. A self-help book will tell you it’s okay to be single and you’ll be happy in life with hobbies, personal achievements, and pets. This is just fuel for the hedonic treadmill that keeps capitalism running. New products and services are always being invented with the purpose of replacing some form of love – whether that’s a meal delivered to your door, or a ride home from the airport. Love is free, but priceless. Love is bad for GDP.
If dating is miserable, you’re miserable. Many people’s stated dating preferences are emotional judo to justify their own unhappiness. If you say to yourself, “I cannot be happy until I meet someone with [insert impossible set of criteria],” you have a great scapegoat for your unhappiness, besides its true source. Don’t blame your misery on not finding what you want. Perfectionism is a refusal to start the journey before you’ve reached the destination.
Beware the ferris wheel. There’s a self-selection bias in the dating pool. It’s full of miserable people who blame their dating life on why they’re miserable. If you want proof, look at dating profiles. I don’t know how men feel about this question, but when I was dating I remember seeing many a woman’s profile demanding men have something better to say than “How are you?” The problem is, there is literally no question more central to existence than “How are you?” Every action every person takes their entire day is in pursuit of affecting the answer to the question, “How are you?” A truthful answer to “How are you?” is guaranteed to lead to a conversation relevant to your well-being. And isn’t that what dating is supposed to be about? So why would someone not want to answer the question, “How are you?” Because they’re miserable. They don’t want a real conversation – they want a source of entertainment. What does this have to do with a ferris wheel? Dating apps are especially full of these miserable people. Dating apps are like ferris wheels: Some people would like to see the lay of the land, but the seats are taken up by people addicted to the ups and downs.
People are not e-commerce items. Dating apps give the illusion of customization. There is no magic algorithm, there is not an unlimited supply from which to deliver your perfect match, and you would be shocked with whom you can be happy. The lines of code are designed to play into your narcissism. Like Narcissus, you’ll think you’re looking at someone else, when you’re only seeing yourself. It’s a person, not a made-to-order blazer.
You do not need to be “challenged.” You hear it all the time: “I want someone who challenges me.” This is usually code for them having an impressive job or education. I get it, you want to be successful and achieve things in life. You’ll do a lot more of that from a foundation of caring and support than from partnering up with a drill sergeant. If you want to be challenged, look for someone so attentive and considerate they challenge your own self-centeredness.
So what if they like Nickelback? Oh, the energy you’d save if you realized similar taste in books, movies, and music is the last thing to look for in a partner.

There you have it – eight harsh truths about dating from me, a former professional dater. I have to admit, dating is mysterious and it’s possible I know little more about what sequence of actions cause love to land in one’s life than does a cargo cult. But since I’m delivering these truths from my privileged position in a happy long-term relationship, I think I have a clear head about it. Think of me as your designated driver: More sober than you single people, but still capable of crashing us into a light pole.

I’ll close with this quote from Roxanne Gay, “I didn’t really learn that I deserved to be loved well until I was loved well.” I hope you find the love you deserve – it may not be what you expect.

Image Credit: Senecio by Paul Klee

The Mind Management, Not Time Management audiobook is here!

Listen to the Mind Management, Not Time Management audiobook free with an Audible trial, or search for the audiobook on your favorite platform.

Thank you for having me on your podcasts!

Thank you for having me on your podcast! Thank you Chris Sparks at The Forcing Function, Dan Pierce at Mentally Fit, and Joanna Penn at The Creative Penn.

As always, you can see a full list of podcasts I’ve been here.