Basically I'm going into my senior year of college and have never went on a date. The weird thing is its not like girls don't like me, I've hooked up with a handful of women I have just never been in a real relationship before. The closes thing I have done to ask a girl out is invite her to a party that I am going to.

Could someone please recommend or direct me to some resources on:

How to know when a girl you know likes you enough that you should ask them out on a date, i.e. the obvious question of how to know if she's into you. All the times I've hooked up with a girl they've always been the one to make a move on me, my philosophy has always been to just be a cool person to be around and let girls gravitate towards me. Now I feel like I am at a point in my life where I want to be able to ask out girls that may or may not be interested in me rather than just let a few of them come to me (this is probably because I've become very interested in one specific girl who hasn't yet really approached me), it sounds obvious but I've realized that if I never ask girls out I will never be able to pick the ones I am really into, instead I will just be able to hook up with girls I am sort of into while hoping the really cool ones maybe find me interesting and approach me.

How to act on a date: should I pay? (I assume I should because I invited them), what are some standard things to do, talk about ect. how long should this date last, does anything above change if you know the girl you've asked out pretty well. Also how to make it clear that this date is just that, a date, not to friends hanging out, but something based on sexual attraction.

I understand that these are things I could google myself but there is almost too much information out there, my hope was someone could point me in the right direction to resources that they think are decent.

TLDR: how do you ask someone out on a date? how do you know if you should ask them on a date? how do you make it clear that you want to go on a date rather than just hang out? where can I find some general first date tips?

Thanks guys, you're all awesome.