LIFESTYLE Relationships  >  Dating Over 50: Learning to Date Again

Dating Over 50: Learning to Date Again

Learning to Date Again
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Congratulations! You have made it more through more than five decades of all the highs, lows, joys and woes of romance and still have enough of a heart left to want to try dating again.

I recently went out with a widower who hadn’t been on a date since 1968 and we shared few laughs about how dating has changed. Following that conversation, I did some research to help all of you who are venturing out into the dating pool again. Here’s what I learned about the new dating etiquette:

Take it easy: Dating in our youth sometimes seemed like a race—biological clock ticking, friends getting married, parents asking us when we were going to settle down. Now, except for the fact that the true finish line is in sight, there’s no rush. Enjoy yourself, take time to get to know someone (and let them know you—the real you—you don’t have time for do-overs) and bring along your sense of humor.

First dates aren’t job interviews: There is no need to reveal everything about yourself right off. A sense of mystery never goes out of style. Asking questions and listening attentively indicates your interest better than yakking away and you’ll learn more.

When listening isn’t enough: Should you Goggle your date? Sure, with a caveat. Don’t believe everything you read. I find lots of people in our generation aren’t fully conversant with the internet—like the fact that any information they put out in cyberspace stays there forever and can be found with only minor digging. That is a good thing when it comes to checking someone out. You’ll want to know if they are who and what they say they are, but don’t go all Columbo. If a man says he’s tall and handsome, but turns up short and ugly—well, nearly everybody lies on dating sites. You are trying to discover the more salient points—like if they are married or they share a home address with Sing-Sing. Check Facebook (people reveal a lot in the “About” tab) and LinkedIn, too.

Cell phone etiquette: Unless you are a brain surgeon on call, turn off your cell phone during a date. (Actually making a show of turning it off while looking deep into your date’s eyes and saying that getting to know them is more important than any call is sure to win you points.) Answering calls or texts during a date—unless it is an emergency– is just plain rude.

Who pays? Whomever asked the other out usually pays, but men over 50 may be uncomfortable with this. If you are the woman, offer to pay for half the check (by reaching for the cash you brought along, not by wrestling him for the check) and then discuss the situation like the adults you are.

Can you have sex right away? If the spirit moves you, go for it—but use protection. Just because a player has silver hair doesn’t mean he/she isn’t still a player. Protect yourself (and yes, women now carry—and offer—condoms.)

After the date: Two antiquated rules are (1) The man shouldn’t call the woman until three days have elapsed to avoid looking “too” interested and (2) The woman should never call the man at all. Call/email or text if you are interested (but don’t be a pest—everyone is busy.) I once sent a man two-dozen daffodils after a satisfying evening and ended up in a very long relationship. (He wasn’t embarrassed. He actually bragged about getting the bouquet.) Don’t become a stalker, but if you’ve got something to say, don’t worry about communicating via text, cell or email; those are just modern methods of communication and thank-you’s never go out of fashion.

Careful about sexting: Look at what happened to Anthony Weiner. Don’t get carried away with the first surge of sexual interest. Keep your photos/videos and erotic emails to yourself until you feel very secure in the relationship.

Clam up about your financial situation: If you happen to be one of the lucky ones who has a tidy nest-egg or profitable investments, play that information close to your vest. Gold-diggers and scam-men (and women) do come in all ages.

Can you meet someone to date online? Absolutely! Two of my Baby Boomer friends actually just got married that way. In a future column, I will tell you all about what sites are best for us over-50 folks, how to write and post an ad, and a few tips and tricks to keep you safe in the world of cyber-romance.

Is it okay to hookup with a younger lover? (If I said ‘no’ here, I’d lose half the male readers right away.) Yes, if younger is your thing and you’ve got the temperament, energy level, and possibly body and/or wallet for it—be my guest. But don’t be courgar-ish and desperate. Realize where you stand in the scheme of things and try to love where you are standing. (Personally-speaking, young men require way too much time holding my stomach in, but to each his own.)

Keep your heart open: Yes, we have all had some disappointments (and some real heart-crackers), but you are never “too old” to date (no matter what your family or society says.) Finding someone to laugh with and love, at any age, is one of life’s greatest gifts.


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