Shy Simon

I wouldn’t call myself a shy person. I mean, I’ve never struggled to keep conversation with people I meet, but I’ve recently encountered a problem. For whatever reason, every time I see a girl, it’s like my brain and feet freeze. I simply can’t go up to talk to them. Any tips on breaking the ice?
Simon, via email 

Shy Simon

Great question, Simon – and thanks for sending in these photos! Unfortunately this “ice breaker” dilemma is a feeling many men have experienced since… well, the ice age.

Some people will tell you to have a few conversation starters up your sleeve, but I believe that getting over the hump requires something greater than a couple of cheesy pick up lines.

The Internet age has unfortunately produced the electronic shut-in. Blah blah, combination of factors go here, but what we have is a whole generation of people who don’t know how to start a conversation. Well friends, here’s a few suggestions to pry yourself out of that wallpaper:

Dance anyway! We hear over and over that “I don’t know how to dance.” You know why everybody says that? Because nobody knows how! So why don’t you invent it? Go to a club where you’ve never been seen before, don’t even talk to anybody, and just dance, dammit! Like there’s a gun to your head! Try it three times, and you’ll never be uncomfortable again. Now watch others and learn how.

Shy Simon 2Practice striking up conversations daily. Any trivial thing. In the elevator, waiting for a bus, or standing in line at the check-out, you can just practice at least speaking to strangers. Just make a funny little comment to no one in particular, and whatever the response is, live with it.

Attend local social happenings in your community. This can be a local garden show, a meeting of the neighborhood association, whatever. The idea is not that you’re cruising for a date, but that you’re just getting socialized.

Volunteer! Work at a soup line or shelter, get involved in your community. You will do good work, you’ll have to socialize at least a little bit, and you’ll never find anybody less intimidating to talk to than a needy teenager – or another volunteer.

Shop second-hand. Thrift stores, flea markets, and garage sales all have these things in common: they’re less formal, more casual, and everybody’s chatty. You’ll meet some of the most interesting people while you both browse the vinyl records in a box for twenty-five cents in somebody’s yard.

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