Karen Yankosky and Philippa Hughes have been friends for more than 20 years. They met as undergrads and have seen each other through two divorces and one bout of breast cancer, with lots of laughter along the way. They also host a weekly podcast about dating and relationships. Recently, by e-mail, they pondered life, love and the pursuit of partnered happiness. Here are some edited excerpts.

Karen Yankosky: I’m 44, happily divorced, and I take full advantage of the privileges of being single: I generally do what I want, when I want and how I want – and my looks haven’t deserted me yet. But in my most honest moments, I have a nagging fear, knowing that at any moment, my looks or my health could go. And if either or both of those things happen, I’d rather they happen with my person — my life partner, as they say — at my side. It’s hard enough to find great companionship as it is.

Philippa Hughes: I feel the same way! 

When I was in my early 40s, I had a friend my same age who complained incessantly about how difficult it was to date. She felt she was entering the years when women become invisible to men. She was a beautiful woman who’d never had any trouble attracting men. But as she got deeper into her 40s, she said that men weren’t asking her out as much. At least not the young, good-looking ones she’d been used to dating. Never mind that she was their same age when she was dating them.

At the time, I wasn’t very sympathetic. I was dating a lot, often younger men, and I couldn’t figure out why she was having so much difficulty. She and I were the same age, so I figured age could not be the problem.

I have developed more empathy since then. Maybe I couldn’t see dating from her perspective because I was lucky to have hit the genetic jackpot with my Asian skin. Thank you, Mom! Now that I have started to see crow’s-feet and droopy bags under my eyes, I am starting to worry that even my Asian skin won’t be impervious to time and sun damage. Maybe she was right!

Last year, I dated a guy who was eight years younger than me. He was super-hot, and women would frequently compliment me on having such nice arm candy. Then one day, he suggested I moisturize my chest, because that was a spot that got a lot of sun and therefore was susceptible to premature aging. He then pointed to the signs of impending wrinkles on my chest. I reminded him that this sort of thing happens when you get to my age, so if you’ve got a problem with dating an older woman, you should not date her. Goodbye!

That was an easy breakup for me, because I never saw us together long-term. But it got me thinking about what my life would be like without a partner. Maybe I should stop stoking my ego by dating younger men. Maybe I needed to snag an age-appropriate life partner soon, while my Asian skin was still holding out!

The reality is: Men are attracted to younger women. We can hold up examples of older women who find love, but that happens rarely enough that I am almost embarrassed at how excited we get when we hear about it. It feels a like finding a unicorn.

Karen: Forget the unicorn, I’m freaking out about chest wrinkles now!

People who know me well sometimes joke about what a wide swath I cut, age-wise, when it comes to dating. Pre-divorce, I dated someone 18 years my senior on and off for about four years, someone 11 years my junior for nearly two years and someone seven years my junior for nearly a year. I married a man 12 years my senior. Post-divorce, I dated someone 14 years younger for two months. And lately, I attract men who are my age or older. It could be that I’m invisible to younger men now, and if so, that’s okay with me.

But I do still feel a somewhat age-driven fear about finding, long-term, “my person.” I never had a biological clock, but my companionship clock has been ticking loudly since my 20s. And by “my person,” I’m talking about the one who’s supposed to be in the foxhole with you, who makes you the top priority in his/her heart. Most of the time, your friends and family have their persons, or their kids, or whatever, so they’re happy to do a cameo appearance in the foxhole, but you can’t expect them to embed.

I definitely have a full, busy, entertaining, amusing, weird life, and I’m happy. But I also wish I had my person, both for immediate and long-term purposes. Certain boyfriends have been my person, for a time, so I’m aware that, with the right company, I’m just a little bit happier. (Conversely, the wrong companionship is waaaaaay lonelier than any solo-ish-ness.)

The good news is my companionship clock is a Timex. That thing has had the crap beaten out of it — dashed expectations, full-blown heartbreak, deception (no death yet) — and it’s still ticking. So even though I worry that as I get older, the pool of men who find me attractive may get narrower and shallower, I still view this whole question very optimistically. Having found great companionship before, I have no reason not to expect to find it again.

Philippa: I’ve been wrestling with the word “companionship.” You and I already have that, with each other and with our close circle of friends. We “get” each other, we love and trust each other. I think we are craving something more than companionship; we are craving intimacy.

As much as I love you and my close friends, we don’t have the kind of physical intimacy we would have with a partner. We don’t have the kind of intimacy that happens in the conversations you have in the small hours of the night with your naked arms and legs tangled together. Or in the early morning when you wake up next to someone with gunk in the corners of your eyes and drool trickling out of your mouth, all your flaws exposed in the sunlight, when you talk and laugh and tell each other how much you love each other anyway.

And most important, it’s in these moments that you share your emotional flaws, every terrible thing about yourself. It feels awkward and weird at first, and then he puts his arms around you, and you feel light and free.

If this person with whom I share such intimacy makes a great companion, then all the better. But I do not want just another companion. I have plenty of those. I desperately crave that intimacy. And as I get older, I refuse to compromise by just having one or the other.


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Why monogamy’s not for me

Forget ‘The One.’ Look for One of the Ones instead.