Baby Boomers:
Women & Dating After 50 With Gail Sheehy

By Judy Dutton
Courtesy of Match.com's Happen magazine


The author of Sex And The Seasoned Woman reveals what’s great about dating after 50—and how to boost your romantic mojo no matter your age.


Question: In your new book, Sex And The Seasoned Woman, you interviewed over a thousand women over fifty—and found that contrary to popular belief, their dating and sex lives are better than ever at this age! Why is that?

Answer: Many are divorced and their kids are grown, so they’ve jettisoned a lot of heavy freight—and are loving it. One mantra I hear from them over and over is “I don’t want to defer.” They were always making allowances for their husband, looking out for their kids, and accommodating bosses and clients. Finally they get to fifty and say, “There are some people I need to please and want to please, and the rest can go fly a kite. It’s time to nourish myself.” They want to go the spa, the gym, volunteer, go out with girlfriends. They don’t want to give up those things and therefore are often not looking to marry again, at least any time soon.


Question: But if you’re newly divorced, isn’t it tempting to jump back into a serious relationship because it’s familiar?


Answer: Absolutely. That’s why I think women should generally wait two years before they even consider committing to a serious relationship. Otherwise it’s easy to seek a safe harbor and really not give yourself a chance to grow. Women this age need to learn how to be alone with the new identity they’re creating. You’ll be more attractive, more confident, and less likely to transfer your sense of loss to someone who may not be able to carry it.


Question: What dating advantage do women in their fifties have that younger gals don’t?


Answer: They’re emotionally more stable. Sure, their hearts can be broken, that will never change, but they have perspective. As one woman I interviewed said, “Losing a man is not devastating. You save devastating for cancer.” By the time you’re fifty, you know the difference.


Question: But what about menopause? Doesn’t that put a damper on women’s sex drives?

Answer: No way! It’s all about attitude, attitude, attitude. Some women’s attitude toward menopause is “Oh my gosh, intercourse is getting more painful” and they give up. But if your attitude prompts you to research what you can do about it, you’ll find out how to revitalize your libido and make intercourse comfortable through treatments like vaginal estrogen.


Question: Why are so many older women dating younger men these days?


Answer: These men were socialized in a post-feminist generation and aren’t threatened by accomplished older women—on the contrary, these traits are attractive to them. My sense is, women over fifty seem to match up best with younger men or men five to ten years older because men in this age group don’t feel huge pressure to prove themselves. They like having an accomplished and sassy wife.


Question: So should women over fifty avoid men their own age?

Answer: Men their own age might not be their best match. Those men are likely looking for younger women who can restore their sense of being virile and still make them feel like they’re master of the house.


Question: What’s the hardest part about dating for women over 50?


Answer: Everybody I talked to has a fear factor about getting naked the first time in front of a man. This self-doubt about their bodies can inhibit some of them to such a degree that they won’t date. My theory is you just have to get out in the middle of the road and date. One woman I interviewed had met a man online but refused to see him in person. He kept pressing her and finally she said, “I can’t meet you because I’m big.” He said, “I’m big, too. My deceased wife was big. I like big. Please meet me.” And she did. He became her “pilot light lover” who re-awakened her sexuality.



Brooklyn, NY-based Judy Dutton is the executive editor of Happenmag.com and has written for Cosmopolitan, Maxim, Redbook, Women’s Health, and other publications.

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