I Started Dating Again at 39. Here Are 21 Things I Learned About Men

When I was about to turn 38, my partner broke up with me. We had been together for five years and had bought our first home together six months previously. Overnight, the future I assumed I would have—marriage, children—imploded, and I was left to pick up the pieces. I might have been devastated, but I was also a millennial woman who had read Eat Pray Love at an impressionable age, so I knew what to do next.

Firstly, I went to Thailand on a yoga and wellness retreat, followed by hours and hours of therapy. Then I decided to do the most terrifying thing imaginable. I decided to get back on the dating apps. I went to Paris for June 2024, changing my Hinge location, and over the next 21 days, I went on 28 dates. I repeated this experiment in London, New York and Rome, and I learned so much about myself, but I also learned a lot about men…

I Went on 28 Dates in 21 Days. Here's What I Learned About Men (And Myself)

1. I had seen the ugly comments online, calling women ‘expired’ and ‘past their prime’ once they hit a certain age. I had been afraid that at 39, I would either be mocked or completely overlooked, but most men never brought it up; the only one who mentioned it as a concern was the one who was older than I was. If you’re in his dating range on Hinge, he doesn’t care, so you shouldn’t either.
2. Some men will make you listen as they recite their poetry to you after you’ve had sex. It will be about his divorce and will include an analogy about swans that you won’t understand. It is very important that you do not stay.
3. French men are obsessed with the Eiffel Tower and will insist on showing it to you. A friend posited that this was the Emily in Paris effect, but by my third week, when man #280 asked if I had seen ‘her’, I wanted to scream.
4. How will you know if you’re dating a billionaire? He’ll tell you, along with photos of the private jet, the penthouse overlooking Central Park, and the estate in Hawaii (no confirmation whether a doomsday bunker was built underneath).
5. But other wealthy men will challenge your assumptions by being both generous and discreet. I dated men from all kinds of backgrounds, with wildly differing jobs, and in the end, their bank balance was the least interesting thing about them.
6. You can’t always tell who you will be attracted to—I did not have high hopes for my date with Theo*, a slight, floppy-haired man who had a great love of classical music. But when he kissed me on the banks of the River Seine, it blew the top of my head off.
7. You should always kiss them, just in case. You’ll know within five seconds if there’s physical chemistry between the two of you (or if they kiss like they’ve just discovered their tongue and are determined to make the most of it).
8. Don’t fall into the trap of thinking that chemistry is vanishingly rare; that’s how women get dicktamised. Of the 28 dates I went on in Paris, at least four made me go weak at the knees.
9. The man who gives you butterflies isn’t necessarily the one who is good for your nervous system. I learned this with Rob*, who was so emotionally unavailable that he baulked at being asked his middle name. I would wait for his texts with bated breath until I realised that, as Samantha said to Charlotte in SATC, “If you were 25, that would be adorable, but you're (39) now, so that's just stupid.”
10. 10. French men will look at their phones, realise it’s 10 pm and suggest you go for dinner, and you’re not allowed to shout THAT’S BEDTIME, YOU LUNATIC.
11. Men who say they want a relationship aren’t necessarily ready for it. Intention and emotional capability are two different things, and it’s your job to differentiate between the two.
12. There are kind men out there. Not perfect men, or even your man. But buying into the idea that all men are trash will only become a self-fulfilling prophecy. Look for the good men. What you seek, you shall find.
13. Just because they’re not The One doesn’t mean you can’t stay in touch. I met so many interesting people in Paris; I was determined to keep a few. One texts me whenever he is in London so we can have lunch. Another man sends me a 15-minute voice message once a month to update me on his latest dating sagas.
14. I was convinced that my time with Zach* would turn into something more until it turned out that his incredibly demanding job, family commitments and gruelling travel schedule would always take precedence. Know what you deserve and be prepared to walk away if they can’t meet it.
15. Men are just as capable of catfishing as women. Very quickly, I realised that I, a 5’9” woman, was actually six feet tall — who knew? In Paris, I met a man who claimed to be 37, but when a grey-haired pensioner lurched towards me, I knew I’d been fooled.
16. But there are also the men who cannot choose a good photo of themselves. André was one of the most handsome men I’d ever seen in real life, but he looked like a garden gnome on his Hinge. Why do perfectly attractive men select profile pics like it’s an active campaign of self-sabotage?
17. Men love explaining their niche obsessions to you. I am now an expert in pickling and the workout regimen of a professional boxer, both entirely against my will.
18. The idea that having sex on the first date will make men respect you less is archaic and, in my experience, untrue. The kind of man you want to date is not concerned about what your ‘body count’ is. Nor does he care if you are more successful.
19. Try not to look for villains. I was upset after Oliver ghosted me, but I soon realised that he simply didn’t have the emotional capacity for a difficult conversation. Isn’t that sad? We’re all just people trying not to get hurt again.
20. Trust your instincts. The morning after the first date with Oliver, I wrote in my journal that he was cute, but I had felt slightly uneasy at times. Your body is always trying to talk to you.
21. Dating is so much better when you stop treating every date like an audition for the role of Husband. Prioritise having fun and pour into yourself — your friends, your career, your hobbies — just as much as your love life. Build a life so good that a man has to earn his place there.