How To Date At Midlife

Our Q & A with an expert—the author of Love at Second Sight—shares some wisdom on how to succeed at love.

By Chelsea Kaplan

aving trouble finding success as a midlife dater? Below, Mason Grigsby, co-author of Love at Second Sight: Playing the Midlife Dating Game, weighs in on the missteps you may be making and how to refocus your energies in a way that will bring you a fulfilling relationship.

Why are there so many single baby boomers currently on the dating scene?

The divorce rate is now 50 percent for first marriages and inexplicably, even higher for second marriages, even though logic says that you should know what you want the
To meet people, try special-interest groups.
second time around. Currently, there are 42 million singles over the age of 50 in America. So for those people who believe there is no one out there for them, they need to think again! It may take some effort and you may have to exert some energy and get out of your habit of sitting around waiting for something to happen, but you really can meet someone.

In what ways is midlife dating a game? How do you recommend it be played?

The game of midlife dating is actually a metaphor for understanding the basics and how to get it right in your next relationship—learning how to play it correctly the second time around. With midlife dating, just as with any life experience, learning from past mistakes is essential to playing better in the future; with midlife dating, you need to learn from your experiences and make better relationship decisions the next time around.

Playing the midlife dating game is different for men and women; the mistakes made the first time around need to be revisited, and playing on the second try requires paying more attention to the habits of the people you encounter. This time, be sure their habits and qualities fit your lifestyle. Many women, for example, in their youth dated men who they felt had some bad habits, and they believed they could change them with marriage. However, those women later found out that they were mistaken, and they learned that you can't change another person’s habits. This knowledge — at least in theory — should teach women to play things differently the second time around. Ideally, they’ll move on when they encounter this situation again later in life, avoiding the lost cause of trying to fix someone.

What about men at midlife—how should they play the game?

Men often entered into a marriage because they found a woman with whom they had a great sexual relationship and who fit their social background criteria. And, this may be a startling revelation for women: As men mature, they recognize that things like common interests are more important than an intense physical relationship and a woman who fulfills a laundry list of surface qualities. The second time around, most men play the dating game differently and pay more attention to these deeper, personality-oriented qualities as opposed to the more superficial ones they revered in the past.

What are some of the most common mistakes made by dating baby boomers? How can they avoid making these mistakes again?

Key mistakes made by women over 50 include coming across as too needy, being too abrasive—many self-help relationship books tell women to be aggressive, which is often interpreted as abrasive by men. Typically, men in midlife are seeking a woman who is easygoing and not competitive. This does not mean that women should be subservient, but they need to be considered fun to be with. In fact, this was the number-one quality men reported that they looked for in a mate. Women must learn to be less intense about relationships and just relax when it comes to discussions or activities. Just remember this is a first date; it’s not that big a deal!

As far as men are concerned, the number one gripe I’ve heard women report is that men spend most of the time on the first date talking about themselves. This often happens because men who have not dated in a long time are very uneasy and insecure on a first date. As a result, they talk about themselves because they don’t know what else to do. I recommend that men ask a date questions; try to find out her interests, likes and dislikes, but to be careful not to make it sound like an interrogation. If she is interested, she will ask questions and give you plenty of opportunity to talk about yourself. My advice for a woman faced with a seemingly self-centered date is to give him a second chance. If you like him and this seems to be the only problem, cut him a bit of slack; he may relax and actually ask questions about you. If not, you haven’t lost anything but a little bit of time.

Any other tips on playing the dating game better at midlife?

There are many ways in which midlife singles can be better at playing the dating game. Both the men and woman I interviewed when writing the book indicated that they highly value honesty; many have experienced bad situations in which a former partner lied. Therefore, I always recommend operating honestly when re-entering the midlife dating world.

Another big problem with many men and women is that they withdraw and don't get out into the social world. No one will knock on your door looking for a relationship—you need to get out and make it happen for yourself.
Guys: Take an interest in your date!
A key error many make is not being social when they do go out there. If a person you meet casually says hello, respond! Many, many men and women reported meeting their next partner simply because they responded when someone said “hello”. This can happen in an airport, an elevator, a restaurant, on a bus, a ballet, a play or at any other social event. One woman even told my co-author and I a story about beginning a relationship in a grocery store! As she was standing in front of the pastry section, a man asked her, “Do you like chocolate cookies?” When she said yes, he grabbed a bag from the shelf, opened it and offered her one.

What are some of the best ways to meet other singles over 50?

According to my research, the number-one answer received from both men and women to this question was special-interest groups such as book clubs, hiking groups, tennis teams, skiing clubs, etc.

Also, many, many people had great success dating online. Often singles ended up with new friend instead of a romantic relationship, but not one of the 1,000 people interviewed expressed that anything “bad” happened when dating online.

What are the keys to finding lasting, meaningful midlife love?

Most midlife singles say that the key is meeting someone with whom they have common interests and someone they can trust. The most popular responses as to why their first marriage ended were poor communication, different goals and priorities, and the fact that they married too young. Ultimately, I advise being honest, knowing what you want, making sure you understand everything about the person you are dating, but most of all, making a commitment to yourself to get out there and be open to new encounters—no one will find you while you are in front of your television or while you are reading a book.

Chelsea Kaplan is deputy editor of
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