At Midlife, Dating Like a Prom Queen

Our bodies may not be as lithe as they were in our 20s — so what? In the dating game, midlife confidence more than makes up for it.

By Sherry Amatenstein, LMSW

One of my regrets when I married at 20 (not a typo) was that I’d never know what it was to be sought after by the opposite sex. During my brief career as a dater I’d felt shy, awkward, unattractive, and lonely. No wonder when I’d met someone who, for whatever weird reasons, desperately wanted me, I allowed myself to be swept along even though I wasn’t sure how much I wanted him. And I didn’t ask myself the right questions, like whether his quick-to-flare temper and propensity to make up outrageously creative lies when cornered made him poor marriage material.

After the marriage fell apart (I know this shocks you!), I quickly fell into other long-term relationships. I had a fear of dating because along with that availability came the potential to be rejected.

Or so it seemed. Well into my 40s I found myself once again unattached and in no hurry to change that status. And suddenly the skies seemed to be raining men. Men who were available and wanted to spend time with me even though I was no longer quite so young and fresh.

In our age-obsessed society, much ink is being spilled on the plight of boomer women who feel insecure in the love arena, who fear men their age are looking for hot young chicks, thus are bitter, miserable, and resigned to a long, lonely, solitary second half.

Yet according to Diana Kirschner, PhD, many women find dating at midlife more gratifying — "like night and day" compared to their younger days. The New York-based author of Love in 90 Days runs workshops that empower women to date three men at a time. She explains, "An older woman can have more fun than a teenager because she’s much more grounded, which makes her more present and less anxious." If one guy doesn’t like her, all it means is there’s an available slot for another.

Sheila Kramer’s dance card is certainly full. A Hamptons-based graphic designer, she’s in the midst of a midlife dating renaissance. The 56-year-old divorced mother of two, who’s taken Kirschner’s workshop, explains, "None of the three men I’m dating feel like long-term potential and none are sexual relationships but it feels great. I call the shots. I know what I’m doing, and what I’m looking for."

She spent the five years in between her marriages feeling frumpy and unpopular, and desperately wanting another husband. But during her latest period of singlehood, that longing has morphed into a feeling that, while it would be nice to find a partner, she needn’t be lonely in the interim. To feel more confident, she hired a makeup artist to teach her the tricks of the trade, got a glam haircut and a sleek new wardrobe, began working out regularly, and lost 15 pounds. Kramer says happily, "People who haven’t seen me in two years wouldn’t recognize me."

So the idea is to have what Amy Boswald calls "a delayed teenagehood." The 57-year-old, twice-divorced mother of 14-year-old twins says, "I skipped dating when I was younger. I had a boyfriend in high school, then married my college sweetheart, and later met my second husband at work. I had a pretty sheltered upbringing and everyone I dated was pretty much like me — same ideologies, hobbies, etc."

What caused her turnaround? She explains, "Going to online dating sites and discovering people with different backgrounds, faiths, and values has given me the opportunity to get over certain prejudices and ideas." Adds the Denver marketing executive, "I’ve been attracted to men I never would have given a second look at before. There’s something freeing about not feeling every date has to lead to forever."

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