One thing you might want to consider doing is getting used to walking around with a half smile on your face all day long. It may sound a little weird but it will make you seem more open and friendly, and everyone will be wondering What the hell does this person have going on that makes them so happy? If you get used to half-smiling all the time, how hard could it be to shoot a stranger a strong smile?
The smile I'm talking about is a kind of "I just found 20 bucks on the ground and this cool breeze is really satisfying my soul" kind of smile. Just a content, lazy smile, the way a cat would smile if they could while napping in the sun.
Your smiles don't seem genuine because they aren't. When you actually smile, small muscles pull the corners of your eyes. This is really hard to fake.
My suggestion would be to have a funny joke, situation or other trigger to think about when you want to shoot someone a smile. This will cause you to genuinely smile. And if its an attractive woman, just think of how happy she'll be that you sent her a smile. It will likely make her day.
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