Definitely not. Granted, you can’t do the “chat” thing for months before asking a person out, but establishing some commonality then going for coffee is a super way to get together. When I did the internet dating thing, that’s pretty much how it works, you make contact, chat online, get to know the person a bit, then go out for a low pressure date like coffee. That’s how I met my wife, right down to the first date being at a coffee house.
What I think really helped me was just getting to the point where I didn’t really care one way or the other if a particular woman rejected me or if a particular date went well or fizzled. You don’t need to be every woman’s friend, there are way too many out there to keep track of, they will move on as well.
There’s one thing I wanted to mention about asking women out because they smiled at you. I was raised to consider smiling in general to be polite and meaningless. Indeed I was taught, not smiling in public or when I look at someone is rude. A friend of mine who’s half my age was taught the same thing. There have been times when I’ve been walking down the street and men who are complete strangers have, out of the blue, told me to smile. I can’t tell you the number of times I’ve considered starting a Pit thread about how smiling at someone doesn’t mean I want to meet him/talk to him/have wild monkey sex with him. It simply means, as a rule, I acknowledge his existence within my field of vision. A generic smile alone doesn’t mean I’m interested in someone, although a somewhat broader than usual one or a smile accompanied by some other body language might. Here’s how to tell the difference. If it’s the exact same smile a girl’s giving to everyone else in the room, it’s probably not an invitation to hit on her.
I had a well-meaning English teacher tell me in High School not to smile at people in cities, because they will think I’m a whore.
I’ve gotten into trouble for smiling at the wrong guy a few times, but most men are aware of Siege’s rule and take my smile at face value, so to speak.