Do I Still Have It? The Trials Of Over-50 Dating

If someone had told me in my 20’s that this is where my love life would be in my 50’s, I would have escaped to a remote island, a convent, or a so-so marriage. Being single at 53 is not for lack of trying. It’s not for lack of desire, or being unwilling to make compromises and bend. I’m a busy and active gal – passionate about my career, and with a great group of (single and married) close friends. But I’ve always preferred being in a relationship with a man vs. taking the solo route.

Yet, I want a healthy coupling where we enhance each other’s lives: one that’s based on respect, fidelity, affection and open lines of communication. Little did I know when I was doing the scene at 23 that this might be as rare as a snow leopard sighting. I used to fantasize about Mr. Right, but now I’m apt to conjure up the Being There Dude: a solid male I could wake up to, shop at the market with, and fall asleep on his shoulder while watching TV. Maybe we could raise a puppy together.

In the past year, I’ve come out of a long-term relationship which I believed would lead to marriage (beware of separated men: it ain’t over till it’s over), and so, back in the trenches, I venture out on those infrequent occurrences known as a date. The French have it right in that Plus ca change, plus c’est la meme chose, but there are some pointed, and surprising differences.

THEN: You want to look pretty for your first date, but not too sexy and give the wrong impression.

NOW: Make sure he sees you still have your figure or you won’t get another shot.

THEN: On second thought, hint at a bit of cleavage.

NOW: Wear a scarf to hide necklines.

THEN: Make your hair clean and shiny.

NOW: Cover the grey, girl.

The beauty magazines confuse us all, and the youth culture is daunting. Most of us can never look like the hot 50-somethings (Nicole Kidman, Cindy Crawford, Michelle Obama), and there isn’t much advice for dating over 50.

THEN: Add a bit of eyeliner for added allure.

NOW: Lose the heavy eye-make up or you’ll look like a drag queen.

THEN: Carry birth control.

NOW: Even if you’re still menstruating, what are the chances??

THEN: Wear nice underwear in case things get unexpectedly heated.

NOW: Consider Spanx to block the tyrannical tummy.

When you date in your 50’s, you’ve accumulated so much experience (and baggage), that conversations can be tricky — sometimes it’s best to just shut up and drink:

THEN: You talk about universities you’ve both recently left.

NOW: DON’T mention college. He’ll ask when you graduated.

THEN: You mention you had an early marriage and it “taints” you.

NOW: You’ve never been married and he wonders what the hell is wrong with you.

THEN: You’re witty and have an “edge.”

NOW: Careful not to be cynical…

The bottom line is, getting older has its advantages. The men who looked like baby-faced nerds in college, start to look damn good after 40. And being someone’s second wife can be preferable: let him make the mistakes on the first one, and come to you from a place of appreciation. Also, because their sex drive is not what it used to be in their salad days, they have come to value intimacy more.

Why am I still dating? I’m told I have many qualities, inside and out, by men I admire, yet I haven’t had much luck in the long-term romance department. Perhaps, I’ve been caught in the post-feminist zeitgeist: we’re a generation unsure of our feminine/masculine roles – wanting our independence, but yearning to be part of a couple.

Maybe too, I’ve haven’t chosen well. As evidenced, the things that are important to me now, weren’t back in my youth, and I probably dismissed some really great guys. I’ve had to wrestle with demons that were guiding me to unfulfilling, frustrating choices (surely continuing patterns of my childhood), which I have since learned to identify, and hopefully, transcend. Maturity teaches us we can’t live with regrets – the only remedy is to move forward.

Perhaps the biggest advantage to aging is we are now more comfortable with who we are, and generate better self-esteem. Sure, we would’ve liked to have it while in possession of our young, nubile bodies, but there’s always a trade-off, and any man worth his salt will tell you that confidence is far more sexy than double-D boobs. Especially at 53.