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Find Love In Your 50s and 60s

Think it’s nearly impossible to meet someone when you’re over 50? Nope. Check out where these folks found great dates.

By Elise Nersesian

Trash talk
“One time I met a man cleaning up trash in a local park. There, among banana peels, fast-food wrappers, and napkins with bubble gum stuck to them, we fell for each other. We even had our first kiss in the park after he asked me for a date! Doing charity work is not only fulfilling, it gets you out there in the world. And you learn from the get-go that he has a good heart, simply because he’s there in the first place.”
—Sheila, 57, Boston, MA

Love Lesson: Step outside your comfort zone and get involved in community
“If you meet doing charity work, you know he has a good heart.”
service. If you don’t know where to start, volunteer in your own town (at fundraisers, park clean-up days, church food drives). You may meet an empathetic sweetie—or at least make a new friend who will widen your social circle of class acts.

Raise your hand!
“I attend lots of audience-oriented events—from book readings to TV-show tapings. My advice is: Don’t be afraid to spark up a challenging conversation with someone at a lecture or reading. You never know—the feisty discourse could lead to love. I was an audience member on The People’s Court and was seated next to a nice-looking woman. After the show, we walked out together and fell into a natural conversation about the verdict, which we vehemently disagreed on. We continued bantering out of the TV studio, onto the street, and over dinner later that night!”
—Matthew, 60, North Ft. Meyers, FL

Love Lesson: Always put your opinions out there when you’re at an event that encourages conversation, even if you’re afraid the other person won’t agree. You may find out you share the exact same sensibilities. Even if you don’t, though, you’ll get to know each other quickly and will learn fast whether he or she is a good listener—or the dreaded talk-over-you type.

Trip out
“One time I met a man on a cruise to Bermuda—we kept running into each other. Being on a boat together made it difficult to miss one another… not that we wanted to! We struck up a conversation about the awful lasagna in the buffet line and ended up in a long-distance relationship after the cruise ended. Vacation is a great get-away from daily life, and since everyone is relaxed, it alleviates the pressure of dating in a normal setting. What better way to get to know someone than in warm weather amongst friends and fun?”
—Penny, 63, San Diego, CA.

Love Lesson: Visiting new places gives you a new perspective on life and can even make you more confident because you’re removed from your normal routine and stresses. Even a quick weekend jaunt with a group of friends or a solo trip to a music or arts festival can help jumpstart your romantic life. And even if you don’t meet someone special, it gives you a great opportunity to try out your flirting skills.

Click in the cubicle
“Work is conducive to romance because in a lot of fields you spend many hours chatting with people. I’m a realtor, and I once met a man while selling him a home. You learn quickly what a person’s tastes are, and often his or her life story—things you would
To branch out, accompany a friend to a work party or college reunion.
never find out at a bar. This relationship — although short-lived — made me realize that everyday situations can bring about romance.”
—Marie, 54, Lynchburg, VA

Love Lesson: Well, first, a caveat—in some workplaces, office romances are a real no-no so check your company guidelines before you get your flirt on. Now, even if there are no prospective dates in your office or you just don’t want to get involved with a colleague, consider your officemates an uptapped social network and RSVP yes to everything from going-away parties to happy hours—you never know what friend-of-a-co-worker will tag along.

Hear it through the grapevine
“Meeting a man in your social circle is smart because you have a good screening system to make sure he isn’t a kook. I had a standing lunch date with a girlfriend of mine, who at the last minute asked if I would mind if she brought her friend along, a navy civilian, who had just returned from Iraq. During lunch, he folded his napkin in the shape of a rose and handed it to me! I felt comfortable pursuing this man because he knew my close friend, and we started dating shortly after.”
—Ellen, 49, Watertown, MA

Love Lesson: Re-evaluate the singles who are already in your life. There could be a match you’ve never looked at in that way. If not, widen your social circle by asking friends to set you up with their pals. And don’t shy away from new situations—accompany a friend to a wedding, a work party, even a college reunion.

Don’t hit delete
“I once met a great woman because my name was on a mass email, and one of the respondents ‘replied to all’ with a clever one-liner. I was having a bad day but her message made me laugh so I responded. Then she did, I did, and so on. Before I knew it, we were sharing anecdotes from our childhood and first marriages! I felt like I knew her so well before we even met—and fell in love. If somebody’s personality shines through in a crowd, don’t ignore it. There could be a connection there just waiting to be sparked.”
—John, 55, New York, NY

Love Lesson: Look for opportunities in unusual places. Email allows you to be candid without worrying about how you look. Whether you add comments to a friend’s blog or try online dating, you may be surprised at how many kindred spirits you’ll find.

Get fit and flirt
“Meeting people while you exercise is great because you know right away that health is important to them. You also know a part of their daily routine, which can provide a comfort zone. One time, I met a woman through a walking group. We got to know each other over the course of a five-mile walk through the city. We got fit and fell for each other at the same time.”
—Michael, 61, San Diego, CA

Love Lesson: Join a co-ed walking group. Chatting not only makes exercise less dreadful, but walking is a low-impact sport, so you’re not huffing and puffing while trying to flirt. If you can’t find a walking group, consider joining a co-ed class at the gym.

Go to an in-house matchmaker
“My daughter took out a personal ad for me in our local paper without telling me and personally interviewed five men she thought I’d click with. Then she set up a dinner for the three of us and strategically left the table. Boy, was I surprised. If you don’t want to do something as bold as a blind date, ask your kids if they have any friends with single parents. It’s worked for a few of my girlfriends who have met great partners this way!”
—Janet, 56, Waltham, MA

Love Lesson: Sure, your grown kids may not come to mind when you think of potential matchmakers, but they know you deserve only the best, which means they won’t pair you up with losers. So let them know you’re open to meeting someone. (Keep the tone light, though, so they don’t feel pressured to play matchmaker.) Who better to set you up than the people who know you best?


Elise Nersesian has written for Redbook, Stuff, and other publications.
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