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What to expect from dating in midlife

Katie Glass reveals the ins and outs of what to expect from the midlife dating world.

When someone suggested I write about midlife dating I balked: “But I’m too young!”. Then I realised – just because I live like a teenager doesn’t mean I am still one. I suspect all single women my age feel like this because mid-life is not what it was.

I thought by my 40s I’d be married and mortgaged, with an Aga, a bundle of children and a dog. Or perhaps like Miss Havisham, who was “scarcely 40”, wearing a tattered wedding dress in a house overrun with cobwebs. Instead, I’m on my sofa, swigging champagne from the bottle, swiping through cute men on Tinder. Again.

Older single women are cooler…and more plentiful

Now, thank god, the cliché of creaky spinsters or desperate cougars has finally been replaced by a swathe of cool, hot, career-focused women – think Mindy Kaling, Germaine Greer, Rashida Jones – awake to the exciting realisation life is better when you’re not tied to a man.

Now there are more single women in their 40s than there have ever been. Between 2002 and 2018, the percentage of never-married women aged 40 to 70 rose by half a million. Amongst women in their 40s it doubled.

There are loads of advantages to dating in midlife. Now, if nothing else, it’s easier. We’re overwhelmed by dating technology that didn’t exist when my dating life began.

Remember when dating apps were new?

In my 20s, I fell for people at my waitressing job or got drunk in a club and went home with them. It wasn’t until my early 30s, way back in 2013, that Marie Claire magazine asked me to try out these new things called dating apps. I signed up for several, marvelling at how they were the straight equivalent of Grindr and “your phone’s GPS technology beams local boys direct to your palm”. At the time I wasn’t convinced they’d take off. Now I have RSI from swiping on them.

Of course, the people you date in midlife are different. The men my age are balder and chunkier, they’re widowers and divorcees and all have kids “who are my world”. Sometimes they’re also more interesting – with fascinating careers, lives lived all over the world, bank accounts that mean we could just run away to Paris for the weekend (and if we could travel, we would).

How young is too young?

Still, sometimes I also find myself creeping down the age brackets. Wondering: “Can I date 35-year-olds? 33-year-olds? 30-year-olds? When do I become a creepy old woman?!”

Now I’ve hit 40, I’m surprised by just how much attention I get from 20-something men, who tell me they’re “desperate to sleep with a MILF”. (Even one who doesn’t have kids.) Being called that would have infuriated me in my 30s; now I find it hilarious. And perhaps that’s the best thing about dating in midlife – you care a whole lot less.

In your 20s dating is an anxiety-fest, fuelled by drunk highs, existential hangovers and panicking: Does he fancy me? Will he call? Am I cool enough/ casual enough/ thin enough for him?

Somehow your 30s are even worse. Conscripted into panic-finding The One, with sex-focused only on getting knocked-up.

Dating in midlife means less stress

Now in my 40s I’m over that hump. The stress has gone. Having taken Gloria Steinem’s advice to “Become the men we wanted to marry”, I’ve got my own career, my own money, my own interests and friends. My sense of self doesn’t depend on who I’m dating or shagging. Which is a luxury only men used to get.

Midlife dating: More carefree

In your midlife, you start caring less. Now I’m not intimidated by getting DTF texts. I’m more confident exploring in bed. Other friends my age feel this way. One 40-something friend tells me she’s desperate to try anal sex: “Before I felt bad about it or thought it was dirty but now I’m much more relaxed. I realise everyone is doing it and I want to try it too,” she trills.

Another friend recently cheerfully told me she’s given strangling ‘a go’ in bed, while another friend, who has always been strictly anti-drugs, knocked back an Ecstasy on a recent one-night stand. “Why not try it!,” they shrugged. Another friend is considering an offer of a threesome but “I’m most worried about getting semen stains on the sofa,” she confesses.

Why is midlife dating different?

Perhaps this desire to explore comes from a sense of feeling in control: Now I’m not worried about being talked into doing things I don’t want.

There’s an element of wanting a last hurrah and to reclaim a youth we didn’t get. Because, like so many women, my friends and I spent our youths being too sensible. As women, we’re enlisted into guilt, into being the caregivers, peace-makers, organisers, who always put our needs second. No wonder there’s an orgasm gap.

Now we’re older, we’re enjoying being irresponsible. Which is why mid-life dating is so much more fun. I’m looking forward to it….

Katie Glass


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