A T pass?

I couldn't decide what to post for Labor Day. A letter? More Love Letters Spam? Updates?
Instead, here's something that’s more of an etiquette problem than a love problem, a letter we wouldn't post on a regular day but is good fodder for debate on a holiday Monday.

We'll get back to real problems tomorrow. In the meantime, discuss love on the T. And … am I the only person who finds Charlie from the Charlie Card moderately attractive? He's got a little Don Draper in him, I think.

I'm a frequent reader and am curious to hear your advice on a conundrum I've been having. I consider myself to be a funny, kind, non-threatening, likable guy in my late 20s, but I'm initially very shy and have some self-confidence/self-image issues. This leads me to have difficulties meeting women, in general.

My question is -- what's the etiquette regarding talking to women on the T? Maybe it's because I'm shy, but I'm always skeptical when a random person tries to strike up a conversation on the T, but is it like that for everyone? Are women generally guarded against a guy approaching them on the train, or is it possible to make friends during the evening commute -- without getting maced?

– Curious Commuter, Saugus

You're allowed to approach a stranger, CC. But if you are rebuffed, please retreat.

You can say, "Nice backpack," and smile. You can say, "I feel like I see you every day. You must work near me." You can simply grin and nod. But if the object of your affection rolls his/her eyes or doesn't respond, that’s your answer. Move away. Stare out the window. Forget it ever happened.
I'd like to think that we're all allowed one chance to make a respectful pass. As long as your body language suggests that you're a shy-yet-hopeful guy who's not looking to steal a purse, you shouldn't get maced.

Just be prepared to move to the other end of the car if you get a dirty look. And don't take it personally if you do. Some people want their commute to be a quiet time. But I'm sure many folks out there would love it if a nice, cute, shy guy said hello during a long ride.

Readers? Are you open to being approached on the T? Is that weird? Is it any weirder than being approached in a bar? What's the trick? Is this harder on the Green Line? Discuss.

– Meredith