When a Parent Starts Dating Again

Question: How should I talk to a parent who's dating again?

There are some situations that are always awkward no matter how mature you are. Having your own father ask you for dating advice would, I suspect, top almost anyone's list. But that's precisely what I found myself doing last Christmas, when I was home for a visit. The worst part of it was, I couldn't even complain. This was a role I had volunteered for.

In the first couple of years after my parents' divorce, I resisted the idea of their being with anyone but each other. But seeing my father lonely was even worse, and after 12 years without my mother it was time for him to move on. He wanted to meet women, but didn't know where to start. So I offered to help him post an online profile.

I didn't know quite what I was getting myself into. Before long, my father was asking me for tips on where to meet women, how to present himself, and what to wear. I suddenly felt like I was the father and he was the son.

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This kind of situation is more common today than ever before. The divorce rate remains celestially high. We live longer and stay fitter until much later in life. "Viagra alone has completely changed the landscape of sex for older men," says April Masini, author of Date Out of Your League. The upshot is that adults in their 20s and 30s will often see a parent start dating just as they themselves are settling down.

So how should you talk to a parent who's starting to date again? How do you deal with the awkwardness and discomfort you'll inevitably feel?

The first thing to realize is that it's natural to feel squeamish when parents talk about dating. Don't feel shy about drawing a line between the subjects you're willing to hear about and those you are not.

Once your parent understands that you're not interested in locker room stories, though, it's time to get over your embarrassment and put his or her happiness first, says Yvonne Thomas, a psychologist based in Los Angeles who specializes in relationships. "You have to accept them as living, breathing human beings who need love in their lives." In fact, she says, it's a good idea to say just that to your parent: I don't want you to be lonely. You deserve love and happiness, and I want you to have a well-balanced life and be fulfilled in every way. "The point is to give permission to your parent to start dating again," Thomas says.

In my case, by helping my father write his ad, I'd stepped up to the plate. After all, dating again is an enormous, frightening step for many people, and lending support was the least I could do.

"Do you think I have to be funny?" he asked me the next day. "Women are looking for a funny guy, right?"

I took a deep breath. "Dad, you're a handsome, intelligent man, you're physically fit, you're basically world-famous in your field. Any woman would be lucky to be with you." As hard as this was for me to say, I knew it gave him the nudge he needed, reminding him what a great guy he truly was. "It's traumatic to get divorced no matter how old your kids are," says Thomas. "You may not feel great about yourself, you forget your best qualities, you feel like you've failed. You're also older, you don't look the way you used to, maybe you've gained some weight."

"Point out any positive attributes you can," recommends Craig Knippers, a clinical psychologist at the Betty Ford Center in Southern California. "Remind them of the successes they've had, and point out that there are lots of people with their same interests who would find them interesting."

Still, he was nervous. He'd pace back and forth on the carpet while I sat on the bed, his Mac on my lap, typing. He felt embarrassed about posting a personal ad online. I assured him that I had done it, most of my single friends had done it, and that it was nothing to be embarrassed about. As awkward as this exchange was for me, I knew it was tough for him, too.

"Bear in mind," says Carole Brody Fleet, author of Widows Wear Stilettos, "that the role reversal feels strange to your parent as well. But they still need your reinforcement, just as you needed theirs when you first began to date."

We posted the profile, and I briefed him on what to expect. "Women online are constantly bombarded with messages, so send detailed messages," I explained. I told him to respond specifically to elements in their profiles. At all costs, he should avoid "winking," a feature that allows you to send an indication of interest without even writing a message.

The next day, he nonetheless "winked" at five women, sending a message that said "So-and-so has expressed interest in you!" with no accompanying letter. He was still feeling too tentative to commit fully to the process. I told him not to expect much response. But as it turned out, all five responded. One of them, a political activist and writer, responded, "I read your profile with appreciation for your sense of humor, accomplishments, and interests."

I felt a momentary flush of pride, then quickly got to business, giving my father advice about how to respond, whether to talk on the phone, and when to set up a date. He listened, but the next day he told me he'd taken down his profile. He just wasn't ready, he said.

Someday soon, he will be ready. Meanwhile, writing the profile was a way to feel closer to him and express the things that I don't always feel comfortable telling him directly—how highly I think of him, what wonderful qualities he has, and how much I care about him. Helping my father with his profile turned out to be a reward in itself.

Answer: Put your parent's happiness ahead of your own discomfort. Communicate to your parent that you want him or her to be fulfilled in every way, including romantically, and give them permission to go out and pursue that. But it's OK to draw reasonable boundaries. Nobody should have to hear details about a parent's sex life, so if the dialogue ventures into territory you're uncomfortable with, say so. Supporting this phase of your parent's life is a chance for you to demonstrate your love and support for your parent during a difficult time—as good a time as any to start interacting as peers.

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