Please Advise: How do I ask out women I meet on the train?

Pin it

I always chat with beautiful women on my commute. How do I take the next step? 

Wise readers,  

Each week, the inbox of our venerable advice columnist, Miss Information, is flooded with queries. And although she makes a valiant effort, she cannot answer them all. To deal with the surplus, we've decided to turn to you. So, don your spectacles and help this guy out. You can give him advice in the comments below, or, if you'd like to share what you wrote with your friends, on our Facebook page.


Dear Nerve,

I've just moved from Seattle to D.C. for work, and I'm trying to meet new people (read: women). 

Just about every day on the metro, I see women who are attractive and seemingly single. Many of these women put up a shield of books or iPods, but lots of them also just sit there waiting for their commutes to end. I have been told I am good-looking, and in social situations, I'm fairly good at starting conversations.  

However, there's an obstacle: I can start a conversation, but I can't take the next step. How do I initiate a conversation that progresses to asking her out for drinks? What do I even say? If I wait until one of us is getting off the train, we won't have time to swap info, but I hate the idea of asking for her number and then just sitting there awkwardly for a stop or two.  

Any advice? In the end, I don't want to come across as desperate or as a player.

 Breaking the Barrier

Got tips? Leave them in the comments. Got questions of your own? Email