Dating Over 50 - The New Rules

Not sure where to meet other singles or what the heck to wear on a date? Heed this advice for grown-ups.

By Beatty Cohan

y the age of 50, most people expect that they’ll finally be kicking back a bit and enjoying the fruits of their labors, ideally with someone they plan to grow old and grey with. But whether divorce or widowhood has thrown a wrench in that reverie, or you’ve just never found your special someone, many fifty-somethings do find themselves single—and sometimes a little worried about it. While it’s easy to feel like a fish out of water surrounded by blissful couples, don’t worry—there are plenty of people just like you who are hoping to find The One. In my experience as a psychotherapist of 35 years, I have helped thousands of men and women of all ages jump into the dating game (not to mention enjoy it immensely!). Here’s my advice:

Remember why you’re a catch
Singles can be pretty hard on themselves, especially as they get older. If you’re feeling a little low, it can help to get back in touch with what’s brag-worthy about
Quit assuming that everyone you know is aware that you’re looking for set-ups, and just tell them.
you. Write down three things you have every right to feel good about, whether that’s your killer wit, incredible cooking skills, or the fact that you can still beat your nephew at tennis. Next, pick one thing you’d like to improve. Maybe it’s time to commit to dropping ten pounds or to treat yourself to a shopping spree to spruce up your wardrobe. Giving yourself a goal to strive for can do wonders for your attitude. Harry, divorced at 57, told me this story: “I always wanted to be a good dancer. My ex complained that I wasn’t a strong enough leader and for once she was right,” he admitted. “So I’ve been taking lessons and I’m getting really good. I feel that it’s a new day and anything is possible.” Remember, it’s never too late to learn something new—in fact, it’s what keeps us feeling young.

Put the word out there
One reason many fifty-something’s phones aren’t ringing is because, well, no one knows you want it to! So for starters, quit assuming your friends, family, and colleagues are aware that you’re looking for setups and just tell them. Don’t be shy, everyone loves playing matchmaker.

Know where to mingle
There are plenty of places to keep your eyes peeled—and I’m not talking about the bar scene or nightclubs packed with twenty-somethings. Parents Without Partners workshops, your local Rotary club, and volunteer groups are teeming with prospects. Go with a friend who can provide moral support—and who will encourage you to talk to someone who catches your eye. Your partner in crime needn’t be single; married people are often very competent wingmen or wingwomen since there’s nothing at stake for them. They are totally focused on finding you your best match.

Do speak up
Always be open to meeting someone as you go through your day. The person standing next to you at the post office, at a museum, or while buying a bagel with cream cheese could be right for you. If you’re on the bashful side, think of it this way: The worst they can say is no. At best, you may be pleasantly surprised. Case in point: John, 62, is dating a woman he met at the dry-cleaner. “I was reluctant to approach her for fear of sounding foolish. After all, I haven’t dated anyone other than my ex for over 30 years,” he says. “But I took the chance and asked her, out and now I think that she may be The One.” Just comment on whatever is going on around
Being comfortable is essential—but “comfortable” does not mean an elastic waistband or something that's been in your closet since the 80’s.
you, whether that’s a comment like, “Gee, I’m not used to seeing this many people here. How about you?”

Wear something age-appropriate but alluring
One dating hurdle I’ve heard again and again is this: “I don’t have a clue anymore what to wear.” Many singles in their fifties often feel like they’re stuck between dressing too young — or old — for their age. “I don’t want to look like my teenage son,” says Paul, 56. “But on the other hand, I want to look current.”

The bottom line is, being comfortable in what you wear is essential. But “comfortable” does not mean it’s got an elastic waistband or has been hanging in your closet since the 80’s. Being comfortable means feeling good—even a little jazzed or sexy—when you look in the mirror. If you’re headed out to an event where you might meet someone and your clothes aren’t giving you that little lift, it’s time to go shopping, ideally with a buddy who can offer a second opinion. Kids and grandkids, while they might mean well, aren’t always the best option since they might not understand your sensibilities; better to go with a friend your own age whose taste you trust and who always looks polished. You can also find a way to adapt current styles to suit your taste so you look stylish without feeling silly. For example, women can wear a camisole but cover it up a bit with a cardigan if they are feeling too exposed; men can wear flat-front trousers—but plain cotton ones, not the stretch-fabric variety.

Keep your date conversation on the positive side
Everyone, especially at this point in their lives, has some romantic baggage in their closet, and it can be tempting to share your war stories while on a date. Resist the urge. Even if your ex-spouse cheated on you or your last blind date was a total bomb, saying so on a date will only make you look bad. As Harold, 51, often complained to me, “My last four dates talked about their exes and how rotten they were,” he recalls. “I tried to make jokes about my ex and was met with stony silence from all of them. Don’t they know what a turn-off that negativity is?”

Learn to listen—and be flexible
Many singles, if they’re rusty on the dating front, or maybe a little nervous, often try too hard to make a great first impression. They blab on and on about what they do, their past, and what qualities they find important in a life-long mate…and leave the other person no room to fit a word in edgewise. It’s a complaint I hear especially often from women: “All he talked about was himself, his work, and cars. When he finally got around to asking me about myself, he stopped listening after five minutes!” So, the message to all singles is this: Quit worrying about what they’re thinking about you and ask yourself, what do you want to know about them? Stuart, a 63-year-old widower, has two questions that have worked wonders for him: “What do you like to do for fun?” and “How do you feel about (fill in the blank)?” It’s OK if you don’t always share every point you want to make. Dating is not a race to reveal all—and if you like each other, there will be plenty of time to say everything you want to say.

Beatty Cohan is a psychotherapist and co-author with her husband of For Better, For Worse, Forever: Discover The Path To Lasting Love.
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