Q: There’s a woman who rides my train every morning, and I’m really attracted to her.
You don’t have to walk up to her one day and ask her out or kill her with an insincere compliment—instead, once you break the ice, you can try to get to know her over time, and from there, judge whether or not making a move is a good idea.
Start by standing next to her one day, and if you can, try to find a way to talk to her that doesn’t feel too personal or direct.
Were you thinking about reading that book she’s had in her hands all week?
Apologize for interrupting, then ask her how it is.
She has appeared on MTV, VH1, The Today Show, NPR, The Early Show, The Bill Cunningham Show; has been quoted in Newsweek, USA Today, The Wall Street Journal, Glamour, and Cosmopolitan; and writes a dating column for The Metro.
It and the other letter are below the jump because it’s fucking creepy in there.
Edited to Add: It’s frankly depressing that this post has struck a chord with so many people, but I’m grateful and honored to be able to help the letter writers and to have given voice to what so many people were feeling.
Unfortunately the demands of moderating this discussion have become overwhelming this week, so as of Monday, August 13th comments are locked. Thank you for all of your insightful contributions and for making this one of the best commentspaces on the Web. He’s about 10 years older than the rest of us on average, divorced with two kids.
Could you not make out the train conductor’s announcement? Then, once the ice is broken, simply introduce yourself—and see how she responds.
You don’t need to be overly forceful with questions or conversation that first day; let her come to you. Even if she doesn’t keep up a conversation with you that morning, perhaps in the days to come she’ll smile at you, wave, or start talking to you in more depth.
Your goal with this first encounter is to just plant the seed that you’re a friendly guy she can chat with if she feels like it.