I’m a man in my 30s and have never been on a date nor had a romantic relationship. I take public transportation to work daily, and I see a couple of women here and there that I want to go and start a conversation with. The problem is that I get very nervous and don’t know what to say. Yes, we’ve all dealt with rejection, including me, and I constantly remind myself that it’s part of life and I have to get over it. My question is, how do I approach women I don’t know and start a conversation? Any advice is very much appreciated.—Shy and Lonely
Dear SAL,
I would encourage you to NOT try to pick up women on the CTA. Not because it’s impossible, but because it’s an advanced move and I worry that as someone with limited experience, you’re setting yourself up for failure.
That said, I DO encourage you to approach women simply to talk to them, with no other agenda or expectations about the interaction. This takes the “rejection” part out of it for now. And these conversations don’t have to be on public transit—talk to baristas, grocery clerks, bank tellers, and everyone in between. This will help you to de-escalate the fear and nervousness you have around talking to women.
What do you say, though?
There are lots of low-key ways to start a conversation with a stranger. I’ll start with the easiest/lowest risk and work up. And let’s use the public transit theme, but don’t feel limited by these scripts. Start each of these with a “Hi” or “Hey” so she knows you’re trying to talk to her.
Situational questions
“Do you know if we passed Diversey yet?”
“What are you reading? Looks engrossing.”
“The drunk guy over there keeps bumping into me. Mind if I sit/stand by you?”
Opinion questions
“Let me get your opinion on something. My niece is turning 10. Do you think that’s too old for a doll? What would you get her?”
“You look like you have great taste. Do you know where I can get [some item of clothing or shoes you’re interested in]?”
Comment on something unique about her
“That’s a great jacket/brooch/necklace you have on. Where’d you get it?” (Or, if it’s applicable: “Is there a story behind it?” Obvs doesn’t work with everything, but at worst, she’ll simply say “No” and you’ll have to come up with another question/comment.)
“Your dog is cute. Can I pet her?”
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“This is random, but you’re cute and I wanted to meet you. I’m SAL.”
The most important tip for overcoming approach anxiety is to talk to as many people as possible —aim for at least five people a day. Doesn’t have to be a long conversation, but just to practice. Rope a friend into it if you’re really nervous, so both of you can practice. Look them in the eye while doing so, and speak loud, slow and clear. The more you get used to talking to strangers, the more comfortable you’ll be approaching women in any situation.
Good luck, SAL, and report back to let us know how it went.
Anna Pulley is a RedEye contributor. Want to ask Anna an anonymous question about love, sex or dating? Email your quandary to [email protected].