Another way of looking at things is "just ask". What's the worst that'll happen? They say no, you lost nothing, gained nothing. But there's a surprising # of yeses out there to be had.

Which reminds me, I once asked this beautiful woman out, not thinking she'd say yes, but she did. We had a good run.

My business partner (an extrovert, where I'm an introvert) put it this way: if you don't ask, the answer is always "no".

Here is the issue though .. as a man, if I am not interested in clubbing, going to the bar, art class, etc. where do I meet women to ask? This was the conundrum I was in throughout grad school. It is really, really hard. As I have aged, I know there is a flip side of the coin, where women also wonder where the "high quality" men are hiding. But it is way too hard.

I do remember in my younger days approaching someone on the bus .. in a friendly, non-creepy way. It didn't go anywhere but we did become friends for a short period. I just don't think it is okay approaching women generally in places like the bus because it is not okay to make them feel creeped out.

Others have said, but institutionalized settings can be good for getting the "vetting" out of the way. Why do so many romances originate in school? Because each and every participant recognizes everyone else is in the exact same position he is -- a subject of circumstance.

Streets, transportation -- these are low-filter interstices. Maximum wariness is warranted, really regardless of sex.

If you're not interested in going to the club, bar, art class -- what are you interested in? Seriously. It's tough. If your hobbies are sticking your head in the sand / introspective study (mine are), you will need to jump outside your comfort zone or else expect some degree of social resignation.

> What's the worst that'll happen?

It depends on how bad you are at following rules #1 (be attractive) and #2 (don't be ugly). If poorly enough, then even a coffee invite will get you fired with a sexual harassment suit following you around for the rest of your life.

> rules #1 (be attractive) and #2 (don't be ugly).

Those are imaginary rules. Physical attractiveness isn't as important as many people think. Charm and confidence are much more important.

> even a coffee invite will get you fired with a sexual harassment suit following you around for the rest of your life.

No, it won't, unless you're actually engaging in sexual harassment.