Daily Life

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The biggest challenge when looking for love

Over the past five years, I’ve discovered some of the marvellous challenges that dating in midlife has to offer.What to write on a Tinder profile? Who to swipe right on? What to say in that first text message? How to deal with the kids? What to wear on a date?

But the greatest challenge of dating at a certain age isn’t who to choose, or what to write. It is far more fundamental. It’s the challenge of protecting ourselves from pain, while staying open to the possibility of love.And it’s hard. It’s the hardest thing of all.

Nearly every woman and man on the dating scene at my age has significant relationship baggage. How could we not? We’ve been separated or divorced. We may have been mistreated by romantic partners. We may have been lied to or betrayed. We have certainly all had shitty dating experiences.

And this can make us bitter and defensive. After all, when you’ve been hurt repeatedly in love, it is rational to build an emotional wall. When vulnerability has led to pain, it makes sense to bolster your defences so that it doesn’t happen again.

Take me, for example. (Really. If you’re cute and well adjusted and smart and gainfully employed, take me now.)

“Are you still in touch with your ex?” I ask potential partners. “How long since you broke up? Are you likely to get back together?” And who can blame me? I have been dumped by men for their most recent ex more times than is statistically probable. It is my own personal Groundhog Day, and I’m concerned about it happening again.


But, of course, it’s not helpful. Men generally don’t like to be grilled about their exes on the first date. And besides, it makes me look a little crazy.

Still, I’m far from the only one who goes into dating braced for possible disaster.

"Sick of princesses and high maintenance chicks!" Men write on their dating profiles.

"If you’re not going to bother answering my messages, swipe left."

"Everyone on here is so fake."

One man asked me in our first text exchange if I took anti-depressants as his ex was depressed and he "wasn’t going there again." Another asked me if I was financially secure, as he’d been "used and abused too many times before."

We women may be hyper alert to signs that the men we meet are "just like the others". We may have our own peculiar deal breakers that reflect our own past hurts. We may be slow to trust, and put up walls between ourselves and potential partners. Or we may give up dating altogether, because "there are no decent men out there".

"Men are arseholes", we text each other after dates. "What’s the point? I hate them all."

Of course, it’s counter-productive, because of the great paradox of relationships. We need to let our guard down to meaningfully connect with another person, but the greater our vulnerability, the greater our risk of being hurt. And the more scared we are of hurt, the more we try to protect ourselves from pain, the less chance we have at connecting.

It’s incredibly difficult to get that balance right. It’s incredibly difficult to open up at all. I have so much admiration for women and men who are constantly putting themselves out there, back on the scene, after hurts and disappointments in love.

And I do it, too. I strive to remain open. I remind myself that there are good men around, even if I’ve met more than my share of the bad. I remind myself to give people the benefit of the doubt, and that I’ve been pleasantly surprised before.

Mostly, I remind myself that if the worst does happen, I’ll survive more pain. It’s better to give it a go and be hurt than to shut myself down forever. But it’s tough looking for love, and it goes far beyond the perils of Tinder.

Working out who to swipe is only the beginning.