Q. There are a few fine ladies that I have the pleasure of sharing my 45-minute morning train commute with. Although I have done nothing but steal furtive glances up until this point, I was wondering what you think is the best way to introduce myself and eventually woo them (one at a time of course). – Dr. Love Train
TN-OK: I actually know a couple who met on the New York City subway, so this is not an abstract question.
It’s great that you don’t want to be creepy, or date all these ladies at once (which could also be filed under creepy, depending on your approach).
I think that meeting someone while commuting sounds fantastic; second only to my dream of meeting someone in the grocery store. It is possible, but not simple.
Your approach should take all the basics of good commuting and polite society and just bring them together. You’ll also have to add a dash of bravado to engage a lady directly at some point.
If there is one that catches your fancy without headphones, start there. A friendly smile as she walks by you on the platform is a good place to start. Try it a few times, maybe also a smile on the train as she passes by.
The first time she might not catch it, but if she notices it a few times she might start to smile back. Single ladies notice gentlemen that try to make repeated eye contact, trust me. On a slow day or during particularly bad weather, you could attempt to strike up a conversation. Weather is always a good topic.
Since you already know she is on your commute often, you don’t have to ask for her number the first time you drum up a conversation. Just a simple weather observation and funny aside could be all you need to lay the groundwork. A first date could always be a cup of coffee or beer as you exit the train station instead of a full-blown evening out.
Commuters that are in their own musical world are harder to strike up a conversation with, but that doesn’t mean you can’t hold a door coming out of a station or smile all the same.
If you feel like the clock is ticking, you could always dig up some courage and just casually say, “I see you on this train a lot, do you work in Midtown/Downtown/wherever the train lets you off?” Don’t ask where she lives because that’s creepy. If she takes the bait, you can then say something about where you work, so it’s a conversation and not just a stalker intro. Again, you don’t have to invite her out on the spot, but maybe just lay the groundwork to ask her out after you chat her up a few more times.
Lastly, check for wedding bands. No use wasting your time on a lady that is already off the market.
P.S. – If your commute involves a bar car on a commuter line, for goodness sake, offer the lady a drink sometime on a Friday evening.