The One That Got Away

"This could but have happened once,
And we missed it, lost it forever".
(Robert Browning)

Mid-life dating is, to say the least, challenging. You spend so many hours each day working, commuting, dealing with kids or elderly parents, doing the food shopping and all the other chores and errands, that you have little or no time to pursue romantic adventures. Yes, you may sign up for an online dating sevice, but before long you've allowed things to drift; you're too busy to even check your inbox. At work, everyone who's even remotely attractive is married. Even if you had the time for bars, your experiences in them have been dismal in recent years.

You seem to be waiting for lightning to strike, and sometimes it actually does---sort of. You see the person of your dreams in the produce aisle of the supermarket, or at an adjacent table at Starbuck's, or in your checkout line at Target. You want to say something, but...you just can't. You're instinctively afraid of looking foolish, or being rejected. So you let the moment pass.

But oftentimes you torture yourself afterward, and, against all odds, desperately try to reach out to that person who exited your life as quickly as he or she entered it. The "Missed Connections" section of Craigslist.org is full of sad stories of lost opportunities, along the lines of: "Yesterday at Trader Joe's. You asked me which wine would go best with chicken piccata. I talked your ear off about Chilean sauvignon blancs, but was too shy to ask for your number. Write to me please".

It IS hard to approach a stranger, or to turn a "neutral" conversation into something a little more personal. Aside from the rejection aspect, we may be short of time, or in a distracted mood, or aware of how sloppily we're dressed, or be otherwise unprepared to initiate a little flirtation. It's a common problem, but fortunately there is a fairly easy solution.

Have some cards printed. Not business cards (you don't want to divulge too much information to a total stranger, no matter how nice he or she appears), but simply cards with your name and either your e-mail address or your phone number. If you're feeling unbearably attracted to the person behind you in the checkout line, but also unbearably nervous and tongue-tied, just take one of your cards out as you're leaving, and give it to the person in question with a friendly but casual-sounding, "I'm in a rush but I'd love to talk to you more sometime. Here's my number. Give me a call".

If you don't hear back, you at least won't be kicking yourself about the one that got away, and you won't be writing needle-in-a-haystack messages on Craigslist. The person may be married, or engaged, or just not interested; whatever it is, you can accept it, and you can't blame yourself for not trying. But if you do get that call, you'll be on top of the world. You'll be proud of yourself for making it happen. And your new friend will be impressed with your initiative, creativity, and self-confidence.

Give it a try. You've got nothing to lose but your regrets.