When it comes to affairs of the heart, we are all beginners. Some of us, however, at least speak with authority. Introducing Shon Faye, author of The Transgender Issue (2021) and the forthcoming Love in Exile (2025), whose advice caught our eye. Contact her at DearShonVogue@gmail.com for your own chance at enlightenment.
Dear Shon,
I just ended things with someone who had ever-diminishing time for me. I’ve since learned, however, that he returned to another ex, and it has been painful to realize he chose her over me. But the larger question I’m left with is: What am I doing wrong? I’m in my early 40s, living in a youth-obsessed metropolis, and the apps are graveyards of forsaken hopes if you’re a bit older or have reasonable (any?) expectations. Given the dispiriting offerings so far I’ve tried to restrict my dating pool to my friends’ friends. Which is unfortunately pretty tiny. I inevitably strike upon some giant red flag. So my question is: Where does a person look to meet worthy prospects these days?
Flailing but Fun
Dear Flailing but Fun,
Your letter displays an all-too familiar spiral, one I’m going to suggest we take a step back from and observe calmly. You have linked two different anxieties together into one concern. Firstly, the end of a specific relationship which has left you heartbroken and wounded. Secondly, a broader freakout about the dating landscape for women who are looking for love over the age of 40. I think leaping from one to the other is a recipe for panic and despair. When I’m spiraling I also tend to link my highly specific present circumstances to a grander social narrative about womanhood, aging, and societal norms in order to make sense of the world and my place in it. Sometimes, though, it can trap me in a pessimistic place.
Things didn’t work out with this particular guy and you have concluded that this is about you not being as good as the ex with whom he’s reunited. Can I suggest another possibility? What has happened here is not about your intrinsic worth (or hers). It’s more likely to be that many straight men aren’t very good at dealing with heartbreak or being single and so they move on to a new “situationship:” (I call it a phantom relationship) far too quickly after a significant relationship ends. This leaves them with an ex they have unresolved feelings for and a new woman who they may care for but whose needs they cannot possibly meet once the shiny phase of new romance is over. If you accept this possibility, it may just be that this is not a story of two women desperately competing for the prize of an amazing man but the story of an emotionally confused man expecting relationships with women to resolve his confusion. When someone goes back to a recent ex, it’s a real sign that they probably had no business starting a new emotional relationship with anyone else.
The fact you became entangled with a particularly confused man doesn’t mean you’re doing anything wrong, but I hear you about the dating anxiety. You ask where to meet good prospects. I turned 35 this year and so I have a taste of the specific issues in looking for a connection once you are no longer a young woman. (Almost instantly, the algorithm on dating apps started to discriminate against me and the number of potential matches my own age declined, which reinforced the tedious social narrative that men only like younger women). We internalise this stuff, too. Societal misogyny tends to make us view youth as a depreciating asset when it comes to dating, which is why in my mid-thirties I see so many single women in a blind panic about not having found the right person (and some settling for the wrong one). We are brainwashed into thinking that our forties, fifties, and sixties may well be a romantic wasteland if we aren t settled soon. It’s all terribly Jane Austen.
In fact, I think not being a young woman is an asset in dating. In my twenties, I had less experience of the world and less wisdom. I didn’t know what my own needs were when I was in a romantic partnership. Year on year, as I become more self aware, mature, and discerning it actually is more rarely I meet men I would want to date. Again, this is good. I am exercising my choices in more informed ways. I might despair that there aren’t better options, but when I am feeling more balanced I can accept that I may well meet someone in a year or two and if I went with the wrong person now I may miss someone more able to truly meet me later. This sort of reframing is necessary to contradict the game-ification of dating that modern technology can promote.
Yes, the older you get, the fewer single men there are around. That’s undeniably true. I think a lot of women struggle with this. We have got a career, good friends, interests, we have learned from our mistakes, had therapy and done the work. We are ready, so where is he? The reality is you have to accept you cannot control who comes into your life and when. A successful relationship isn’t like a career or re-tiling a bathroom or training for a marathon. You can’t will it into being. It requires two people’s readiness and ongoing willingness.
There’s a huge element of luck. Dating apps definitely become harder work the older you are: partly because we just tend to be busier and less patient with the ratio of grim interactions you are exposed to when interacting with faceless strangers. So using your existing social networks for setups is wise, as is making time to meet new people through hobbies, volunteering, parties, or whatever else you enjoy. Be open to new people but don’t turn it into a vigorous pursuit at the expense of all else.
