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The One Big Question I've Always Wanted to Ask Older Women

What they do makes no sense to me.

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illustration of couple sitting at coffee shop drinking coffee
Jared Oriel
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My friend Jane has been married to my friend Luke since we were all 28. She has seen me through two husbands and four, five or six boyfriends. Every time I visit, she asks after my exes as if they are still my friends.

“And how is X-Y-Z?” she’ll say, as if she assumes my exes still walk this earth and that I routinely, casually communicate with them. I never have a calm response, because the truth is, every one of my exes fills me with shame, anger, longing or frustration. I do not say this aloud, since a 57-year-old woman does not want to admit to having the immaturity of a hamster.

I’ve always wondered why women have ongoing relationships with former partners — warm, caring, supportive friendships. Why would you stay close to someone who caused you pain and reminds you of your failures?

Part of the reason I have trouble identifying with such emotionally mature relationships is that I want to exile my exes to Uranus. I tend to pick passionate, destructive, emotionally remote partners. I’ve worked hard to change this pattern, but I’ve largely failed at picking sweet men to throw my heart to.

Unsurprisingly, these Mr. Wrongs make lousy former partners, too. The cheater-hoarder-STD spreader. The rich narcissist. The lover who wouldn’t walk me to my car in the middle of the night in his dangerous neighborhood.

Who would I want to be friends with any of these men?

Honestly, they have not wanted to be friends with me, either.

So that’s my first observation. If you want to stay friends with your ex-partners, pick stable, sane partners in the first place, like Jane did with Luke. But then why would you break up? So much to unpack here.

The first person I turned to for advice was a 65-year-old friend and fellow journalist who had a spicy love life before her 40-year marriage and birth of kids. Three of her former boyfriends came to her wedding! and two proposed marriage.

“I’m the perfect woman to interview because I’m friends with all my exes!” she announced cheerfully when I called. “My high school boyfriend, my college boyfriend, my first job boyfriend …”

My initial question: If these men were solid enough to stay friends with, why did you break up at all?

“The high school boyfriend stayed in our hometown, skipped college and I skipped town and started college,” she began. “Then came an eight-year relationship with a moody, gorgeous guy that was obsessive, stormy, make-up and break-up and make-up and finally broke me after many years. The last boyfriend, well, that one is tough to talk about. That was an amazing love, so sexy — but the future was unreal. He wanted me to convert to his faith and I would never leave mine. I am still in touch with all of them.”

My second question: How can you do that?

“Once you love someone deeply — and you haven’t destroyed each other — that love doesn’t die,” she explains, wistfully. “We had a priceless connection that I never want to sever. Three of them knew my dad — my favorite person in the world who died when I was 31, and a man my own husband never met. These boyfriends of youth — now in their 60s and 70s — are my history holders.”

Sonja Lyubomirsky, PhD, has spent the last 30 years researching happiness at Harvard, Stanford and the University of California. Her research builds a case for staying connected with lovers in a new relationship she half-jokingly calls “Friends Without Benefits.” Currently a Distinguished Professor at the University of California in Riverside and the author of The How of Happiness, Lyubomirsky believes one of the keys to joy is that human connection.

"Deep connection is hard to find,” she explains. “We have lots in common with our exes. Intellectually, emotionally … a shared history and family relationships. Although the new relationship may be painful at first, it’s a waste to not enjoy those connections simply because the primacy of your romantic and sexual focus has shifted.”

Now of course, if an ex was abusive, vengeful or part of a destructive pattern you are trying to break, no one advises investing the time and energy to maintain a lifelong friendship. But if your philosophy parallels my colleague’s — say yes to the exes — the next question becomes: How? What are the tips and strategies to have a fulfilling relationship with ex-lovers and ex-husbands?

How do you stay close to your ex-partners without driving yourself or your current partner nuts? Here’s some advice from my long-married friend whose wedding was attended by men she still loves.

“First, set your boundaries and respect theirs,” she says. “They are Exes, not your Nows. My husband has actually become friends with two of them, and our children are friends, too. I also married someone who is very secure and doesn’t have a jealous cell in his body. So, I get this unusual and fulfilling experience of having lots of different kinds of love and loves in my life.”

She laughs and says that she is also friends with a couple of the exes’ wives. “One complains to me about some of her husband’s annoying habits that I know well, and I tell her, 'Sorry to hear that — YOU married him, not me'."

“Oh,” she adds as a final suggestion. “Don’t drunk dial any of the exes on Valentine’s Day.”

My most recent boyfriend is the only ex I don’t fantasize about putting in a dunking machine. Before, during and after our relationship he’s been kind and generous. He may not be The Forever One for me. But I sure want him to be my friend forever. So let’s end with a toast: Here’s to growing up and not leaving the best parts of your romantic past in the dust.

 Are you friends with any of your ex-boyfriends or ex-partners? Let us know in the comments below.

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