Ya the only advice that makes sense is:
Just ask her. You don‘t have to (and really shouldn‘t ever) ask her if she wants to be your girlfriend. Thats too much commitment to just simply agree to right off the bat, even if you have known her for a long time.
You just ask her point blank if she would like to go to dinner with you, or a movie, or a dance club, or somewhere fun like an amusement park, or mini-golf or something. Or even something that‘s totally un-datelike. Like if you‘re friends already, just ask her out for a day hike, a walk on the beach, rollerblading in the park, a concert, or whatever else you know she‘d be into doing. Just as long as you get her alone and can start giving her that "I‘m interested in you" vibe.
If you really like her, playing cool is going to lead to weirdness later on when you let your guard down and she realises you aren‘t the same guy you were posing as. If you want to try to really connect and develop a solid relationship, then being honest about who you are (with her, and yourself) is the only way to go.
If you just have some strong physical attraction and want to get it on with her, then just play the game. Everyone knows how to play the game on some level. Just use what you‘ve got (car, money, cool friends, good looks, tough guy/ badboy image) you know, whatever.
Women always like to be made to feel like women. They like to be pursued. Trust me, while Joe Nobody is trying to work his way in on a chick through the "friends" angle, even if she likes him and knows he‘s interested, she will drop him like a hot potato for a guy who comes along and treats her like a lady, and makes her feel special.
Joe is using the back door, low risk of rejection, angle. To be right out in the open and simply stick your neck out on the chopping block to ask her out for some alone time shows that you have some b@lls, and that you are so interested in her that you are willing to set yourself up for what is possibly the worst fear of the human race, rejection. (Trust me, this is something that isn‘t lost on women. They know how uptight and nervous you are feeling when you ask them out, and it turns them on)
Unless you are trying to score dates who are obviously way out of your league, you will find that women are very receptive to dating. Even young ones who are only accustomed to dating in a more modern (lets meet with friends for months before we make a move) type of scenario. Closing the deal on a date with a chick you really like is such a rush, I don‘t think a lot of younger guys understand that, since the dating scene has become so timid over the last decade or so.
Keep in mind though you should never ask out a perfect stranger for a date. You don‘t approach women in a bar to ask if they would like to go out to dinner with you for example. You have to get to know them somewhat before you spring the idea that you would like to see them more, especially if a woman is moderately attractive. Attractive women get hit on literaly dozens of times on a night out. They are never going to be responsive to someone who is making a move on her because she‘s hot, she‘s likely been hit on by 30 other guys of all description based on her looks alone. The guy/s who actually talk to her, and (this is important) *make her laugh*, are the ones who are getting her phone#, or maybe even taking her home.
Honesty, self confidence, and humor are the most important tools when it comes to attracting women. If you think that its money, good looks, and coolness, then you are fishing in shallow water, and will probably only end up catching crabs.