I don’t know how to speak to women outside of work

Hi Meredith,

I'm a 30-year-old man who has pushed my social life, in all forms, to the back burner so that I could focus on other things in my life I deemed more important. Over the last few years or so, after getting certain aspects of my life shored up, I decided to get into the dating game and find myself woefully inexperienced and underprepared.

I have tried the dating sites, set-ups, and everything else I can think of, and can't seem to get anything started. I don't even know how to speak to women in a non-work related environment because that is where all my attention has been. For so long everyone who knows me says I'd be a great catch, and I want to believe them. After so many failed attempts and false starts, I am tempted to give up.

I know I don't frequent the places that single women do -- that much is obvious. Do you have any tips or pointers for me? I honestly don't know where I've gone wrong or how to fix it.

– Coming off the Bench, Boston

Your situation isn't so unusual. There are many 30-year-olds going on date after date, looking for the right person. It's not as though they hop on a website and immediately wind up with a partner.

Much of this is about attitude. You have to start thinking of yourself as a normal guy who's looking for a significant other. Everyone is insecure about this stuff. False starts are a part of the process.

Continue to date and, more importantly, spend time with friends out in the world. You don’t have to hang out in bars and hit on strangers, but you do have to see people outside of work. You must develop a rich, platonic social life so that you can be confident of all you have to offer.

Readers? Anything he can do to move this along? Is this about attitude? How can he work on his confidence?

– Meredith