Really good point. OP, I don't know who you are approaching, but a lot of guys make the mistake of going after the women who stand out to them as being hot or sociable and not trying to find things in common with others. There are a lot of girls out of there who get ignored and you wouldn't be competing with a lot of other people for their attention.

Also, many women are looking for someone who wants to genuinely connect with them. It's offputting to realize that a guy only wants someone in his bed, and you're the person who he happened to spot - or that a guy desperately wants a girlfriend, and you'll do. Believe me, it comes across. Some women aren't as attuned to that, but they're usually ones who are happy to find any man who meets traits on a checklist: hot, rich, sociable, etc. Unless you have those traits, you won't succeed with those women anyway.

In terms of connecting with a woman - it might be a little counterintuitive, but it really helps to think that you're evaluating them just as much as they're evaluating you. Conversation is not something you have to endure before you get to ask them out, and it's not a performance you have to succeed at so that they'll say yes. It's a means of finding out whether you guys enjoy activities in common, whether you share some values, whether you have similar senses of humor. You can find out whether she is interesting to you and has a positive outlook, and if she doesn't, then you might want to be the one who backs away and says "It was nice talking to you, see you around."

If you are in a place of genuinely feeling that you like this person and find her interesting, then often she'll feel similarly and want to continue the conversation. This is not where you suddenly fall back into a habit of wanting to impress her, get her in bed no matter what, get her to be your girlfriend at all costs. No, you go out with her, you observe how she behaves in public and around friends, you see if you're still feeling the connection after a few more times of hanging out. You don't rush to get physical, you let it happen naturally - and if it's not there, it's not there. You maintain your stance of evaluating her.

You can do this with several women at the same time - it actually helps to not sink all your hopes into one person.

Also, don't knock girls who just want to be your friend. Friendships can be great, and it's still an honor for another person to invite you into their life as a friend. Opposite sex friendship is not just a means to an end.