Why I Love Dating In My 50s

Men and women share why they believe this is the very best time to date—and how they make the most of it.

By Chelsea Kaplan

hink dating is at its best when you’re in your 20s or 30s? No way! It only gets better as time passes, say these single people. Here’s what they’ve learned… and how you can benefit from their wisdom to enjoy your love life that much more.

There’s no ticking of the biological clock
“Because having kids is usually a thing of the past when
“The pickings aren’t so slim anymore…”
you’re in your 50s, dating in your 50s means you don’t have any pressures of getting married at a certain time because you hear the ticking of your biological clock. As a result, I find that singles in their 50s are much more into entering into a relationship for the ‘right’ reasons, and not just because they think they’re running out of fertile years. It removes a lot of pressure for both men and women.”
—Gail, 56, New Bedford, MA

Getting physical is more enjoyable
“When I was first dating in my early 20s, I really knew nothing about sex; I was so inexperienced in that department. After 23 years of marriage, however, I learned a thing or two. What I love about dating now is that because I feel so much more sexually confident — and even liberated — than I did back then, I really enjoy the ‘getting romantic’ part of dating so much more. I don’t have nearly as many hang-ups and questions as I did back then, so I think it’s wonderful—and the guys seem to think so too!”
—Mary Ellen, 53, Bloomfield, NM

The media smiles on older men
“Back when I was younger, older men weren’t necessarily seen as sexy; the media certainly didn’t focus on graying older males as sex symbols the way it now embraces guys like Harrison Ford and Jack Nicholson. But I feel like being in your 50s in 2009 is no longer considered old, and gray hair is even seen as sexy, thanks to George Clooney. In fact, I find that a lot of women in their 30s and sometimes even 20s find me sexier now than they did back when I was their age. I love that!”
—Abe, 52, New Rochelle, NY

Women become more confident
“I love how self-assured women in their 50s are; they know what they want out of a relationship and what they’re looking for in a mate, and they aren’t afraid to ask for it. Life experience — and learning from past mistakes — brings that, I think. That sense of self-assuredness is so incredibly alluring to me; confidence is just so sexy. I’d take a mature 50-something over an innocent 20-something any day!”
—Dan, 55, Portland, ME

A bigger bank account means better dates
“I have a lot more money now than I did when I was younger, so now I am better able to plan romantic dates at nice restaurants or even take a woman away for a fun weekend
I used to try to adapt to my dates’ personalities.
getaway because I know I have the financial freedom to do so. It’s certainly better than scraping enough money together to barely take your date out for a burger and a movie. I imagine my dates probably like the 50s me better for that reason too!”
—Jack, 58, Carlsbad, CA

Go ahead and say it!
“When I was younger, I was very concerned about making the right impression and being liked. I used to try to adapt to my dates’ personalities. Now, I can’t be bothered with that—I speak my mind, am not afraid to say something outrageous, and just put my cards on the table from date number one. I find that makes dating a much simpler proposition — we either click or we don’t — and guys who get what I’m about do so right off the bat?”
—Donna, 57, St. Paul, MN

Underneath it all…
“I know a lot of women feel like their bodies aren’t as good as they were in their 20s and 30s and before they had kids, but I think bodies with a little character are so much sexier. To make things even better, when I was first dating, the thong hadn’t been invented, and neither had the Wonderbra. Now, though, it seems like they’re everywhere. I’m glad I have the chance to experience dating sexy, mature women in the age of such great lingerie!”
—Craig, 58, Jonesboro, GA

The pickings aren’t so slim
I got married in my 30s, which was incredibly over-the-hill back then. By that time, I think a lot of the good single men my age were married already. The dating pool of single men seemed so small, and I just sort of married one out of sheer desperation because the pickings were so slim. Now, however, I feel like there are an abundant number of single men my age, probably because so many people in my generation got divorced, and many did so around the same time. It’s like an entirely different situation than I knew; there are so many more men out there to choose from!”
—Beverly, 58, Alpine, NJ

Your children become concerned about your dating life
“I have two daughters in their 30s who are married, and now that I am the single girl of the family, I love how the tables have turned. It’s hysterical to hear them give me dating advice, or worry about me finding the right guy, just like I used to do with them! Now I think they understand how I felt about their situations back then and why I used to ask so many questions. It has been a lot of fun sharing my experiences with them and getting advice from them — just the other day my oldest reminded me to use protection! I’ve gotten good dating advice, and it’s brought us closer.”
—Shari, 59, Potomac, MD

Chelsea Kaplan is deputy editor of and regularly appears as a guest on XM Radio’s “Broadminded.” Her blog, “I’m Somebody’s Mother?” can be found at
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