Dating Over 40: A look into one woman’s single frustrations…


It’s a cold, slightly windy day. The kind of morning that has you bundled up and wishing you could still be snuggled in the warmth of your bed instead of fighting your way to an overcrowded cubicle with your name on it. Purposefully strolling into the building you walk straight into a solidly tall piece of green eyed “HELLOOOOOOO there!” He smiles; you return the smile as the two of you continue in this awkward dance of the morning bumps. That’s how my daydream starts.

Then it continues with me saying something charming and witty, and him catching the mischievous glint in my eyes before he returns my verbal volley with something equally witty. We pause and step to the side to allow the rest of the Gophers to hurry along their way to their dismal holes. Our witty banter reveals that we have similar tastes in humor so we can silently acknowledge that the other ‘gets it’.

He’s drawn in by my every woman-ness. I’m not too cute, not strikingly pretty or fabulously fit but there’s something he can’t quite pinpoint about my features that he likes. As we banter about, he’s taking in my neat, sort of stylish attire, my unpolished nails, and my hair although nicely cut has some unruly troublemakers that prefer to draw their own attention by shooting out around my head. He finds it charming, like a Looney Tunes cartoon character. He takes all of this in quickly but doesn’t make an acknowledgment. He gets a sense of the dark side of me but again, can’t quite… pinpoint why he gets that sense, just tha the does. He is intrigued by it.

We realize that we can’t continue to stand to the side of the automatic doors forever, at some point we have to have coffee. He asks for my number, my email, says he’d like to have lunch together since we work in the same building. My wide smile gives him my answer before it’s out of my mouth and we ride the elevator together with a secret now. Discreetly saying “See you later” as he exits the fourth floor.

That would be my daydream.

What usually happens is more like I say something that sounds charming and witty in my head, but what comes out is a garbled mess infused with awkward giggling. That along with the mischievous glint leaves him feeling violated, confused and slightly afraid of this woman grinning at him with her haphazard hairdo that beckons him like Medusa’s calling. He nods politely at me in an attempt to appease whatever dark thing he’s unleashed before rushing past me to meet up with the petite yet voluptuous woman a few feet away. She of the perfectly coifed, impeccably stylish yet age appropriate variety. Or she is the funky, hip girl. Knows how to be brave in her fashion choices, different. The kind of girl that knows how she can get away with mixing stripes and plaid. The kind of woman I never was, never could be – just not part of my genetic make up.

Dating over 40 for women is an interesting thing. The media has glamorized the idea of the Cougar. There is even a show called “Cougartown” in its third season? Successful, independent, beautiful women who have perhaps been divorced, kids are grown and now she is looking for fun. They drive BMWs, Mercedes, Lexus cars, they have money, and they live exotic lifestyles. Younger men would be privileged to have this woman in their lives with her knowledge, her experience. She presents a unique challenge because the man knows she truly doesn’t need him so he strives to keep her entertained and happy. She is intriguing because sexually she is more confident and aware than many younger women. The Cougar presents intriguing possibilities.

If you do a search on “Dating over 40” + “women” an interesting assortment of dating sites and books comes up. “How Not to Stay Single after 40” “Why Mr. Right Can’t find You” “If I’m so Wonderful, Why Am I still Single?”and my personal favorite ” Make Every Man Want You: How to be so irresistible you’ll barely keep from dating yourself!” WOW! Just what I need to date…myself…wait.. Oh yea that’s what I’ve been doing as a single woman. I take myself to dinner, I buy myself flowers, and I treat myself to nice things. I even argue with myself and threaten to withhold sex just to keep it interesting!

I find myself in this odd place in the dating world. Men my age are lookingfor younger women in their late twenties and early thirties. They are both divorced and looking for a younger girl, or they’ve never married so now they are looking for someone to settle down and have a family with. Younger guys find the idea of an older woman intriguing. I don’t fit the Cougar description and let’s face it, at 25 or 30; these guys are still very visual. I don’t have personal trainers, personal chefs or a plastic surgeon to keep me looking like Halle Berry, StacyDash, Diane Lane or Salma Hayek. At this stage, for me to date an older man heis either close to or in retirement. He’s had his kids, wife, and career – now he just wants occasional company and possibly someone to clean the house now and again.

I still love going to music shows, I play Xbox games, I love festivals, and Boston Crème donuts make me a happy gal. I don’t go clubbing, but I still love to dance. Women my age are supposed to dress “age appropriate” but I like those wedge heels and cute tops too! As a woman over 40 I am proud of every wrinkle, grey hair, scar and stretch mark. I’ve earned them. I am more confident of who I am, and more aware of my sensual nature. My experiences have taught me that what I valued at 20 may not have been so valuable. So, gentlemen don’t overlook the ladies who might be checking off the other box on surveys. If you take the time to look beneath the surface you could find yourself pleasantly surprised and in for the time of your life.

A great way to overcome the BS of dating over 40 is traveling with other singles! They say you never really know if a relationship will work out until you go on vacation with your partner.

By stevejuba

Club Organizer and travel lover...

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