Ask Jean: How to Start Dating in My Mid-Thirties?
I would love to get married and have children, but never had a girlfriend before.
Dear Jean:
I am a man in my mid-thirties living in Europe.
I would love to get married and have children, but never had a girlfriend before. I'm socially awkward with women, maybe because I never had a girlfriend before. So the first impression I give is usually terrible. But I am a good person, and I know I would be a good father and husband. Not sure I would be a good boyfriend though, as I have no experience nor much self confidence. Plus I'm too needy.
I don't even know what dating means, or if I can live together with someone else at this point after living so many years alone.
How do I get started?
—Ready but Inexperienced
Dear Ready:
Do you know why I love reading mediocre memoirs?
They give me a ton of confidence. If even they could write a memoir, then one day I could, too.
The problem with most portrayals of relationships is that they show an impossibly idealized version of the truth. Scroll through Facebook and you’ll believe everybody is going on glamorous destination dates. Watch Love Actually and infer that to confess even unrequited love, you’ll need iconic handwriting and at least a dozen poster boards.
Unlearn all of that. The stakes are high, but they become prohibitive if you expect perfection.
Start by saying hi to people (in-person or virtually) and going on low-stakes first dates (coffee; drink; walk in the cemetery). Don’t worry if you feel like you’ve messed up; the other person is probably feeling awkward too. Take things one step at a time and just keep going. Remember that according to the fussy suitor problem, if you’re expecting to encounter n women total then you shouldn’t make a decision until you’ve gone on ~n/e dates anyway.
Many of my friends, including those with lots of dating experience, have also consulted with matchmakers and dating coaches. For instance, check out the website of my former classmate Logan Ury. There are many others like her. Logan has recently written a book How to Not Die Alone; you may want to read that and subscribe to her newsletter too. Another book that I have not read, but recently bought for someone else, is Greg Behrendt’s It’s Just a F***ing Date.
Jean (@jeanqasaur) is a former Computer Science professor turned startup founder and has no business writing a dating column. JeanDate the Advice Column came out of the JeanDate matchmaking project, which led to the shows Zoom Bachelorette and Zoom Bachelor. Submit your questions here.