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Is There a Non-Creepy Way to Ask a Stranger Out?

Yes, you can approach that hot woman who rides your train every morning—without scaring her off. Here’s how.

Q: There’s a woman who rides my train every morning, and I’m really attracted to her. How do I break the ice without looking like a stalker?

A: The only way you’d look like a stalker is if you told her you’re staking out her house, wait for her in the station every morning, have pictures of her pasted on your walls, and, by the way, brought her a granola bar because you know she likes that for breakfast. My point? Relax. If what you say to her isn’t creepy, you won’t look like a creepy dude.

In fact, sharing a commute can actually be a benefit. Because you see her every morning, you have the ability to take it slow. 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. Could you not make out the train conductor’s announcement? See if she caught it. 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. Read her signals. 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.

As you get to know her (which might take a few weeks, so be patient), you’ll get a sense of whether or not she’s dating someone, and probably how interested she is in you. If she drops a boyfriend bomb, then at least you know. If you eventually ask her out and she declines, then at least you tried. And if you successfully start something with a girl from your morning commute, then you’ve renewed the faith in single people everywhere—man and woman alike.

About the Hot Girl: Amber Madison is an author, lecturer, sex and relationship expert and dating coach. 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.

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