Without fail I see the same lovely lady on my way to work from the subway every morning! She always passes by and I can't seem to get up the courage to say anything to her. How do I approach her casually without being that creepy character we all dread?
Please help!
Love,
stalker-i-don't-wanna-be
*******
Dear Stalker-I-Don’t-Wanna-Be,
This is a tricky one. The goal is to be able to somehow put yourself in a casual social situation where you can strike up a casual conversation. The first thing to do is to start smiling at her every time you see here – not in a creepy way but in a “My what a nice morning, hello there nice person” way. Where is this lady going? If you can manage it subtly, you can pretend to be running an errand on your way to work and see where she goes. Window shop, pick up a newspaper, anything that looks like part of your normal routine. Ideally, your ladylove is going to the same place every morning, just like you. Maybe she’s getting a cup of coffee? You can begin to frequent the same coffee shop in the mornings. Smile politely the first few times, and eventually you’ll be able to drop a few words while you’re both waiting in line, which hopefully will lead to a conversation about mutual interests and eventually a date! Be careful not to come on too strong though, especially before she gets to know you. It’s hard to be hit on before your first cup of coffee. Best to start off gently and friendly. You won’t be a stalker because she won’t be able to help but like the nice person she sees every day in the coffee shop.
Good luck!
Love,
von Hottie
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