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Jun 17, 2026

The Case for Giving Up on The One

When The One Isn't Happening

Being a single middle aged woman has never been cool.  Despite huge advances in education, earning power and general badassness, the single woman is seen as not yet realized, incomplete even. To be single at that age must mean something’s wrong. “Why,” we want to know, “is she still single?”

Still. As if it should be some other way. And yet, when she graduated college, the message was just the opposite. It’s too early to settle down. It’s 2020, not 1950. Go to grad school, earn more! Be that #girlboss and don’t forget to Lean In. 

And that’s exactly what she does, spending her 20’s pulling all nighters and fighting her way to the top. She makes bank, buys a sick apartment and summers in Tuscany. Life is great and she’s just getting started.  But instead of congratulations, it’s interrogations. Why doesn’t she have a boyfriend? Why is she so picky? Popular opinion has turned. The very people who warned her not to settle, now demand she settle down. 

But it’s not just them. She also wonders why her life isn’t coming together. In fact, she had always assumed that by this age she’d be married with kids. On the face of it, she has it all. But without anybody to share it with, it’s an empty victory. She wonders, should I have worked less and dated more? The feminist in her balks, but the egg freezing brochure confirms: she isn’t getting any younger.

So in the spirit of making up for lost time, she tries to find the One. Really tries. Following the advice of dating gurus, she writes pages of must-haves and deal breakers. She studies The Rules, carefully evaluates each candidate and when they don’t meet the standard she kicks them to the curb and starts all over again. 

As the body count grows, her stamina wanes. Heart breaking, disappointment mounting and loneliness at an alltime high, she burns out. It’s rough out there and one can only take so much. Her single friends agree, the good guys are gone. So they plan a girls night out and make the very best of it.

But then over lunch she hears about a friend who got engaged to a guy she met on Bumble. And another who, at age 42, is having her first child with a man from Match. In Modern Love, she’s moved by a story of a woman her age who after giving up on love, met her man on Zoom. 

Quietly inspired, she’s ready to get back out there but she’s anxious and weary. The bad dates of the past still sting. What she did before didn't work. She wants to get back out there, but doesn't know how.

As a divorced New Yorker in my 40’s, I knew this story all too well. For years I dated like a demented Formula One driver, smashing into walls and crawling out of the burning wreckage - only to do it again. Every bad date took its toll. A nick here, a chip there, until the gaping hole in my heart forced me to quit.

In the loneliness of those dateless nights, I finally faced my fear of being alone..FOR THE REST OF MY LIFE. It wasn’t them, it was me. Divorced. Single for over ten years. Yes, the time had come for me to accept that I wouldn’t find The One.  I wasn’t lovable. I wasn’t girlfriend material. Or wife material. Or even Instagram material. No number of dates would ever change this reality. I would never find The One.

So what?

No, seriously. So what? What next? I wasn’t ready to join a nunnery or get another cat. I couldn’t imagine a life without romance, affection or intimacy. I still wanted to get dressed up for a fancy new restaurant or indulge in a late night make out sesh. Despite being the oldest I’d ever been, I felt more alive than ever. Finding The One would be amazing, but in the meantime? I’d get back out there, but this time, I’d do it for me.

When I stopped looking for The One, everything changed. I gave myself permission to date not-husband material guys, but who were nonetheless interesting and attractive. Second, I got out of my kitchen and got a romantic life. Sure, it wasn’t the one I’d envisioned but it beat the hell out of waiting around. Some dates turned into wild romances while others enduring friendships. But most importantly, being single felt powerful and enriching. I stepped into my freedom. The middle aged woman was back and cooler than ever.

Finding The One would be great and I don't mean that lightly. What could be better than finding that person? A true life partner would be a dream come true. The other truth, though, is that you can't force it. Love is as much a function of luck and serendipity as it is about putting yourself out there. I will always be open to the possibility of finding The One. But in the meantime? I'm going to live my life.

True love happens when you least expect it. I'm here to show you how to do that.