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64 Dates…But Who’s Really Counting?

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Grace Bennett

By Grace Bennett

Stop the presses: I’ve been on over 60 or so dates in the last four years since my separation and divorce following 20 years of marriage. I’m not boasting in the least about my dating record, and I’ve not really kept exact track. I have been pleasantly surprised though at the minimal effort needed to land a date. A little chatting online, a phone call, mostly to confirm we’re not offended by each other’s voices, and we are who we claim to be, or close enough (lying on the Internet about age and physical appearance has sadly become more the rule than the exception), and we coordinate where and when to meet.

While some find me possible to resist (shockingly enough), overall, setting up the first date? Easy as pie! In revealing a number at all, I am perhaps lamenting the fact that I still don’t have a bona fide boyfriend, never mind a fiance, and that this midlife dating game goes on (and on and on). I did fall in love with one of my very first dates. Unfortunately, he didn’t with me (just really likes me!).  He ultimately offered me a solid friendship as a viable alternative.

Even given that history, and the fact that I am no longer in love, my singleness still seems unlikely.

“How is it you haven’t been snatched up yet?” That’s a “flirt” line on J-Date sent by various men.  That immediately sends me into a tizzy thinking, “You are right! There must be something terribly wrong with me!” What I want to say: It isn’t hard to land dates, but it’s still really, really hard to fall in love. In a mutual way, that is. Instead, I kiddingly respond that I scratch my head over that too. I’m 50–and based on too kind feedback from admittedly biased family and friends–I’m also smart, funny, kind, attractive, educated and accomplished. Did I mention sexy too? Well, I am. Or add modest?  Not terribly, although the seeming immodesty is more a mask for insecurity, truth be told. I have other liabilities as well. I’m prone to headaches and insomnia, lean toward depression and have a notoriously short attention span (when I’m bored mostly) and would never make any best dressed list (although sometimes I hit the mark just fine). I don’t pretend to be whom I’m not–ever. So, take me or leave me, fellas!

Personally, I think I make a perfectly fine and charming date. I can make a man laugh and can hold my own in most conversations, even ones I’d rather short circuit. My Facebook posts about my dates and dating are quite popular, some prompting dozens upon dozens of comments and discussion, which inspires me to write. In using my “real” name on a column, I’m happy to offer enough tidbits to delight any reader, but not the kind of steamy revelations that would have my joint physical custody arrangement revoked.
Now, back to the 64 dates. Yes, it may sound like a high number, but for a midlife dater, who has had profiles on two Internet sites, it is, well, really not that unusual at all.

Quantity is ultimately beside the point, of course. And so is “success” in dating. What all dates and dating have in common are the “live and learn” lessons they impart about human behavior. I hope to continue to write about dating. Maybe, in sharing my experiences, I can shine some light on the incredible vulnerability inherent in being a bit older now and dating anew, the ways in which one’s self image can be sorely tested or, sometimes surprisingly enhanced, how dating changes other relationships in your life, and so much more. Stay tuned.

Grace Bennett is the publisher and editor of Inside Chapapqua Magazine and the soon to be relaunched www.singleandsmart.com where this essay and more “Graceful Dating” stories will also appear.

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