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2. Single 50s Dating

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For those women over 50 who are reentering the dating scene, it’s hard to know what to expect. In many ways, dating men is still the same as when you were in your twenties – communication remains key, intimacy is still awkward – but, with age and experience, comes some key differences.

We asked dating experts, Valerie Gibson, author of Later Dater: A Guide for Newly Single Women Over 50, and Ronnie Ann Ryan, the Dating Coach for Women, about the six things they should know about men in their 50s.

He wants someone close to his age. Despite what Hollywood May-December pairings suggest, Gibson says a man in his 50s wants to date a woman close to his own age. “Most men are looking for women closer to their own age because they understand and have had similar experiences,” says Gibson. “They know women over 50 understand the aging process and men who are like themselves. Men want support from someone who does understand them. They don’t just want a trophy wife.”

He has emotional baggage. Men over 50 have lived a life already — many of whom are either widowed or divorced — which means he might be carrying some residual trauma from his past. “If he has kids or an ex-wife in the picture, the drama isn’t going to get better,” says Ryan. “You have to decide if you want that. A lot of drama doesn’t create love. You have to ask, ‘is that worth it?’”

Gibson puts it another way: “Yes, he will have considerable baggage, but so do you. That’s not to be forgotten. You might have been married and/or have children, so it’s important to remain flexible on these issues.” But, as Ryan advises, be sure you’re still his priority.

He craves emotional support. Men who find themselves single in their 50s have often been married for many years, so they continue to desire the companionship and emotional support they once shared. However, his longing for closeness might not be all what it seems. “Men like and appreciate feminine support,” Ryan says. “They’ll look for emotional support with a woman and she’ll think, ‘oh, he must like me,” and often times, he just needs the emotional support. He will pursue her through text and online just for that. The woman will then assume they are in a relationship, but they’re really not.” What to do? Clarify your relationship status, stat.

He might be old-fashioned. Men in their 50s come from a time when it was expected of them to make the first move. “Let him ask you out, contact you again for the next date and be the pursuer,” advises Ryan. If you enjoyed his company, let him know. “Tell him you had a good time and thank him for choosing a good restaurant or whatever he did,” says Ryan. “Appreciation is important. And offer a compliment – tell him he’s funny, easy to talk to – whatever comes to mind.”

He wants to get intimate. “Men in their 50s do enjoy sex. A lot of people think men and women over 50 don’t enjoy it, but it’s not true,” says Gibson. However, Gibson says it’s vital to communicate what you’re looking for whether it’s a relationship or something more casual. She also notes the rampant STDs within the 50+ age group. People over 50 are having multiple partners without using protection, because many are not used to using contraception, such as condoms.

Ryan advises to hold off on intimacy until the relationship is monogamous, or at least the sixth date, if you’re wondering whether he will stick around after the deed. “Watch for consistency in behavior,” she says. “What he does is what matters most, not what he says he’ll do.” And keep in mind that what 50-year-old men want in bed is different than younger men.

He might have health issues. “A lot of women don’t think about health issues. They think they’ll meet the next George Clooney. He’s going to be fit as a fiddle and all these dreamy things,” says Gibson. “But men over 50 do have health issues, and some of them are quite serious. You may come across diabetes, heart problems, erectile dysfunction…You have to ask questions and decide what suits your needs and desires.”

Singles Over 50 Dating Websites

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