Dating After 50: The Roles Have Reversed

Women & Relationships

(CNN) — The 20-somethings: They’re that odd species with lightning-fast fingers capable of texting, e-mailing, chatting on a cellphone and watching television — simultaneously. And they’re hip — oh, so hip.

A bit too hip for me. No, I’m no cougar. At my age, I could never date a 20-something. For one thing, I’m still mothering two 20-somethings. My girls are doing quite well, mind you. They are in committed, serious relationships with commendable young men.

And their mom? She’s playing the field.

Here’s some advice for unattached boomers: Beware the 20-something in your own home.

When you are a 50-something parent who’s dating, with grown kids around, land mines abound. Those millennials are hip all right — hip to your dating missteps. They’re miles ahead when it comes to the ins and outs of modern dating.

So far ahead, our roles seem to be reversed.

I was a single mother during most of my daughters’ teenage years — that delicate time when things can turn perilous in a heartbeat. Instinctively, I felt that I had to be tougher than most other moms — the moms who had husbands around.

When my daughters were going out for the evening, I would pepper them with questions: “Where are you going, exactly?” (Most of the time they had no plan. They simply wanted to hang out — just like I did every weekend at their age.) “Who is coming with you, exactly?” (Their girlfriends, of course. However, if they got lucky, some cute boys would show up. But they certainly weren’t going to admit that.)

There was so much to worry over and warn them about: drugs, unsafe sex, violence, drunk driving. I could only hope they’d trust their instincts with strangers and even friends — especially with young men.

They knew I was vigilant.

“Don’t lie,” I would say. “You’ll get busted.”

Some lessons were bittersweet, like: part of growing up is having your heart broken. It’s inevitable. You build a more loving heart that way.

I once described raising teenagers to a friend as: “Careening down a hill, at 60 miles an hour, in a car with no brakes. Blindfolded. You do the best you can to steer the thing and pray you don’t crash into anything.”

To this day, my kids complain about the curfew I imposed: 9:30 p.m. starting in 8th grade and 11:30 p.m. in 10th grade. “Nobody except us had a curfew,” my eldest, Nora, told me recently. Her look said it all: “Mom, you’re a freak.”

A freak who fretted when they stayed out til 4 a.m. without calling. (Thankfully, this was rare.) Who warned them to look out for being followed, kidnapped, or worse. “You’re so paranoid! It’s because you work in news,” they would say. Yet, they listened.

Somewhere between fending off teenage angst and hitting my latest midlife crisis, my world got turned on its head. Now, I’m the one asking for advice and my kids are the ones doing the worrying.

Online dating? They’re seasoned veterans who were online dating long before I started.

“Be careful to meet new people in a public place,” Nora told me. Both Nora and Sara, my youngest, offered valuable feedback on my profile and photos.

Getting dressed for a date? “Not too dressy,” Nora warned. “You don’t want to look like you’re trying too hard.”

My daughters had urged me to get into online dating. “You’re a hot mom, go for it,” Sara said. After all, they’d managed to meet a few nice boys online. “We tried to set a good example for you,” she added, with an air of deep wisdom.

Sometimes, the girls will call me in the evenings when I’m out. They worry when they haven’t heard from me for a while. “Are you out on a date?” was the message from Nora. “Call and tell me how it went!”

Oh, and horrifyingly enough, my daughters aren’t beneath trying to figure out my sex life. (I so did not want to know about my parents’ sex lives. But that was in the prehistoric era, apparently.) The girls can’t bring themselves to ask me directly, so they work on deciphering clues together. How many dates has she had with that guy? Did they go away together? Has she met his kids?

Most of the time, I enjoy discussing my dating escapades with my daughters. But clearly, I can’t tell them everything.

I live in mortal fear of the question: “Mom, are you having safe sex?”

Deciding when to introduce a new man, even to 20-something children, isn’t easy. But there’s a difference between bringing every Tom, Dick and Harry home, and letting them know Mom’s friend is more than just a friend.

There is a way to do this right. Go slowly. Don’t introduce the other person until the idea of your seeing someone becomes familiar to them. In other words — don’t overwhelm them with it, but don’t hide it, either.

If you are on good terms with your 20-somethings, talking about dating can be a fun, shared experience.

One word of warning: if you’re thinking about “sexting” your latest hot date — don’t. Especially if you have a tendency to leave your phone around with 20-somethings at home.

You’ll get busted.