Dating Again Over 50?

See how your hopes and experiences stack up against those of our panelists—and listen to how they handle sticky situations.

By Elise Nersesian

any of us were raised to believe that by the time we were in our 50s, we’d be happily married, maybe even with grandkids on the way. But today, more and more baby boomers find themselves still dating… or dating again. Listen in as our four panelists and two experts discuss the dating process at this age. See how your own experiences compare—and learn a new trick or two to find dating success.

The Panelists:
Linda, 57, has a 12 year-old son
Rebecca, 60, has a 34 year-old daughter and 26 year-old son
Mark, 51, has two daughters, ages 16 and 14, and one 17 year-old son
Lewis, 54, has a 16 year-old son and an 18 year-old daughter
Katherine Chaddock, co-author of Flings, Frolics, and Forever Afters: A Single Woman’s Guide to Romance After 50
Evan Marc Katz, author of Why You’re Still Single: Things Your Friends Would Tell You If You Promised Not to Get Mad.

Finish this sentence: Dating at my age is….

Linda: …Challenging—and interesting.

Rebecca: …Comical and scary.

Mark: …Difficult.

Lewis: Goal-oriented.

When it comes to dating, would you like to settle down or have fun playing the field?

Linda: I’m divorced, and I just broke up with my boyfriend a month ago. So I’m dating again. My goal isn’t to find a husband—I never say never, but I’ve done that already. I’m just looking for a boyfriend.

Rebecca: I’ve been dating the same man for five years. We have no plans to get married soon. But it would nice if we did. He’s happy with our lifestyle so I’ve learned to live with our situation the way it is.

Lewis: I would very much like to get married. I got divorced two years ago, and I’m actively dating. I like being in a relationship.

Mark: I’m out there meeting women, but I’m not necessarily looking for Mrs. Right. I want good conversation and laughs. And if marriage happens, it happens. I’m certainly not actively searching for it.

“This stage in life is meant to be enjoyed!”
How do you communicate these goals to the person you’re dating, and how soon?

Rebecca: I’m not a direct person so I let the other person know how I feel by steering the conversation around to philosophy in a general way. I talk about my life in a manner that lets the other person know where I stand on dating. But I don’t ask him direct questions. People share what they want in their own time, and I don’t like to put anyone on the spot. I’d rather keep things light until after we’ve had a few dates under our belts.

Lewis: I’m not abrupt, but during a first date, our pasts will inevitably come up and I’ll say something like, “I’m divorced and I’ve been looking to meet someone who wants to re-marry. What about you?”

Mark: I try to keep everything light for a few months before discussing goals. If two people are going to get serious, it has to happen naturally. There’s no point in deciding whether or not you want to get involved with somebody before you really know them.

Evan Marc Katz: I suggest a series of phone dates first to bring up important issues before you meet face-to-face. Figure out if you’re on the same page in term of goals before you set up an actual date.

There’s a big trend of people your age not wanting to marry. Any idea why?

Linda: The financial ramifications of divorce can leave people gun-shy about the idea of marriage. What if it doesn’t work again? To merge your money and assets with someone is a risky decision.

Rebecca: The emotional upheaval of marriage can be exhausting for someone who doesn’t want big changes in this stage of life. And life is a lot simpler when you’re just caring for yourself.

Lewis: I’d imagine that for many, it may be hard to trust their instincts again if they’ve been through a divorce. You thought you had it right the first time, and you were wrong.

Evan Marc Katz: When you’ve been on your own for a long time, it can be hard to shake up your routine to accommodate another person. And many feel that they’ve been burned by marriage once, so they’re not eager to try it a second time.

Katherine Chaddock: Women have become very independent, financially and personally. They’ve also found that companionship, closeness, and love can happen without matrimony, so they don’t necessarily need marriage to be happy. In addition, baby boomers are the first generation to have experienced genuine male-female friendships. That didn’t happen much for those born before World War II. Back then, a relationship was dating or nothing. But boomers grew up interacting with people who they’d never date but who made great pals. That experience ultimately made it easier for them to feel fulfilled without getting married.

Of the people your age who do want to re-marry, what do you think the reasons are?

Linda: It’s human nature to want to share your life with someone. It’s so much more fun to go through life with a partner, a best friend.

Rebecca: It’s comforting and romantic to know that there is someone who loves you so much that they made a commitment to stay with you for life. Romance doesn’t die with age!

Lewis: When you’re used to living with someone for more than half your life, you often want that lifestyle back right away. You’re used to thinking in terms of two people, and taking care of someone. That’s why most men get re-married again so quickly after being widowed or divorced.

Mark: At our age, you have less job pressure which leaves you more time to focus on romance or companionship, so you end up putting more effort into finding someone.

Evan Marc Katz: Simply put, people love being in love. Love is like a drug—no matter how old you are, you want and need it. And at the end of the day, regardless of how old you are, no one wants to be alone.

Any advice for people in their 50s who are out there dating?

Linda: It’s important to know what you want, so there are no mixed messages. Figure out what you need before you face the dating scene, so you don’t become swayed by someone who isn’t necessarily the best fit for you.

Mark: This stage in life is meant to be enjoyed. If someone isn’t right for you, you can still appreciate the person as a friend if you truly enjoy his or her company. There are a lot of people out there who could be a good fit for you, so don’t settle.

Katherine Chaddock: My advice sounds anti-feminist, but it relieves you of pressure: Make sure he has a good time, and stop worrying about you. Before you know it, you’ll have a good time too. The dating scene is a little bizarre and strange at any age, so just have fun with it. Don’t dwell on one bad date or one that’s clearly going nowhere. Just enjoy the process.

Elise Nersesian has written for Redbook and other publications.
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