I’m a 42 year old woman, newly single. I’m just re-entering the dating fray for the first time in many years, and I discovered very quickly that I have no idea how to identify men my age who are single and looking. They sure seem to be scarce, compared to when I was in my twenties! I’ve chatted up guys who turned out to be gay or attached - they were just extremely friendly/chatty, which I occasionally mistake for an interest in me. And I’m too shy to laugh off any misunderstanding with a comment like, "Well, if you have any single brothers or friends, here’s my card!"

I’m dating online, but I’d also like to meet people in other ways.  Yes, there are the singles events, the frozen food aisle during off-peak hours, etc. But for other situations I may find myself in - elevators, gyms, coffee shops - do you have any suggestions on how I could strike up a breezy, innocuous conversation and still be able to "out" single men?  The "Wow, nice jacket - did your partner pick that out for you?" line doesn’t seem too subtle.

Thanks very much for any insights. 

Enjoy your blog, loved your book.

Linda

Love your attitude, Linda. It’s tough out there, all right, and the healthiest approach is to do exactly what you’re doing. A combination of online dating, singles events, and real-life interactions, all of which create the greatest number of opportunities to meet single men.

That said, it’s not your job to “out” single men.

Because single men have been socialized well enough to know that it’s their job to initiate conversation with you. And if they don’t, they’re going to go home alone AGAIN. I’m not suggesting that this is a biological imperative or that nothing good has every come from women asking men out. Still, I’m a big believer that your primary job is to create the opportunity, not to seal the deal.

Your primary job is to create the opportunity, not to seal the deal.

Check out this short clip from a presentation I made in which I discuss how women can create opportunities with men. It’s at the very end of the five minute montage and it starts with “So if you want to meet a guy at a party…”. To sum up, it’s not your position to ask him out. All you have to do is make eye contact and smile. This gives him  permission to come over without being afraid of being shot down. Because that’s every guy’s concern, especially nice guys. We HATE feeling like fools. We HATE rejection. And we’d just as soon not even approach you, since it’s easier to go home and say, “Man, I wish I said hi” than it is to put our fragile egos on the line. The only way to get an insecure guy to come over is to let him know it’s going to be okay if he does.

Rachel Greenwald discusses her proactive approach for women in her book, and my friend David Wygant’s book “Always Talk to Strangers” is also illuminating, although it’s more written for men. But it sounds like you really have two questions, Linda – you want to “out” single men and you want to find pithy pick up lines as well….

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