Got The Midlife Dating Blues?

Is your love life not going the way you’d like? Consider this wise advice from a woman.

By Jane Ganahl

ell the truth, middle-aged single women: How many of you have found yourselves in this situation? You’re at a party, chatting with a man you’ve just met, and there seems to be a connection. The subject of age comes up, and you, feeling good about yourself, note that you are now pushing 50. He smiles, notes that he is the same age. You chat some more, and then he excuses himself to get another drink. And never comes back.

I don’t imagine you’re feeling so good about your
When you’re most authentically yourself is when you’re most attractive.
self now.

Women can expect little hits like this when she reaches what’s known as “a certain age.” Blame it on our culture that worships youth. Since my book, Naked on the Page: The Misadventures of My Unmarried Midlife, came out earlier this year, I’ve heard from countless single women who empathize. Many of them say they went from turning heads to not even focusing eyes; they became invisible. I’ve written about how few men over 50 actually want to date women the same age. These little annoyances are hard enough to take, but for some, the aging process has become downright insulting.

My friend Wendy Merrill, a 50-ish drop-dead gorgeous writer, was aghast when her much younger boyfriend shrugged off the idea of protection during sex because “women your age can’t get pregnant, right?” She finally gave him the pitch when he told her: “I want to marry someone exactly like you—only younger!”

“I told him, ‘Good luck with that’ and was out of there,” she sighs. He’s lucky she didn’t pop him one!

No matter how fabulous, smart, capable and caring you may be, such encounters can leave you reeling from the blow to your self-esteem.

“There is intense media pressure to always be a flawless 25,” says San Francisco psychologist Linda Thorson. “And it can create a lot of turmoil in older women. We realize we are not sweet young things anymore—more like faces in the crowd. It’s a difficult transition. But it’s possible to use the confusion as a trapeze bar, to lift us on to greater things.”

Easier said than done, right? Not necessarily. Here are some building blocks you can use to reconstruct your self-esteem—and your life.

Remember your passions—and revisit them
“What middle-aged women can do if they have a dip in self-esteem, which so many of us seem to experience, is this: Rather than try to ‘fix’ themselves, they should enjoy themselves—and rediscover what nourishes them,” advises Nicki Michaels, Professional Certified Coach (, who is “over
Rediscover your passion—and indulge it!
50 and loving it.” She says that the midlife years ought to be a time of revisiting youthful interests—or trying new ones. Painting or stock-car racing—why not?

“Women this age should look back on their life before they had a family, or gave themselves over to caretaking others, or were dumped by a man or had an empty nest, and rediscover a passion—and indulge in it! Often, that will take their minds off the little wrinkles, bags and bulges, and lead to a healthier outlook on life.”

Flirt from your soul
According to Thorson, women of a certain age are at their beguiling best. “They’re smart, savvy, and out there in the world.” So when confidence flags, she recommends the age-old balm of flirting.

“It’s true that size and shape are a part of any first impression,” she notes. “But even more important in a woman’s attractiveness is whether she’s awake, alive and engaging. It’s in her smile and her eye contact. Her attitude, her playfulness, her sincerity, and her genuine interest in the other person.”

But, she adds, know yourself first. “When a woman is most authentically herself, that’s when she is most convincingly attractive.” So know your strengths and put them out there!

Tweak your style
By this age, most women have developed their own style. But if the mid-life blues have you down, try on a different color. Or several.

“I tell my clients in that age group to step outside your box a little bit,” says style consultant April Shen ( “My clients who are a little older tend to get stuck in a time warp from the time they felt really beautiful. And the makeup and skin care they used then are no longer working. If they can’t afford to hire someone to do their makeup, I suggest that they go to a makeup counter and ask to have their makeup done. And I advise them to stick to softer tones, more neutral, and get away from the dark eyeliner and such. You want to soften the lines around your eyes and mouth—not draw attention to them.”

The neutral rule does not go for clothes, however. “If you’re used to wearing neutrals, step it up a bit and try a color,” suggests Shen. “If you wear brown, try a rust or pumpkin. Color always makes you feel good and can be a little pick-me-up. Another thing that’s flattering for any figure is wearing an open neckline or v-neck sweater. It shows a little skin.”

Set a fitness goal
At this age, fitness is not a vanity pursuit—it’s an important life-lengthener and health stabilizer. Gina Pell, described as “San Francisco’s most glamorous Internet executive,” is CEO and founder of, an online shopping and lifestyle guide. The “almost 40”-year-old is well-versed in beauty treatments, but says, “The high only lasts as long as the treatment.”

Instead, she says, “The biggest self-esteem booster I’ve found is training for a sporting event. Anyone can go to a gym to lose weight, but making a commitment to see a trainer a few times a week, pushing yourself out of your comfort zone, and struggling through the process of making your body strong enough to finish a challenging event does wonders for the confidence, not to mention you end up with a body to bounce quarters off of. It’s such a powerful feeling and so mood-elevating.”

Do something good and the self-esteem will follow. One thing conspicuously missing in these conversations about beating the midlife blues? Plastic surgery. As Shen noted, “There are ways of changing your life without going under the knife.” And, agrees Michaels, happiness must inevitably come from within. “When we change our perspective on life, we are changing our life from the inside out, and that’s when change is most meaningful and long-lasting.”

So how does one change perspectives? Pell has a simple suggestion: Volunteer. “The best way to feel young and beautiful is to do good things in your community. Hang out with seniors—they tend to be very interesting, anyway.”

Find something you feel passionate about that’s outside your daily realm—foster homeless pets for your local humane society, drive meals to shut-ins, plant trees with an urban forestry group. Or, take a page from my own playbook and volunteer for a beach clean-up. Your blues will lighten immensely, knowing you did something good. And you might even meet a hunky surfer or two. It’s a win-win for all.

Jane Ganahl is author of Naked on the Page: The Misadventures of My Unmarried Midlife, editor of the anthology Single Woman of a Certain Age, journalist of two decades, and co-director of San Francisco’s Litquake literary festival.
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