I've technically never been on a date...Help? [19/Male]

Let me explain: I've only been in two relationships and both were with my best friends at the time. My first ended mutually since I had to move and the other ended horribly after being together for 11 months. Each time I've never really asked them out, it's always just happened. My last one happened when we kissed on her bed and from there we just went around as boyfriend and girlfriend.

So what I'm asking is what is the best way to take a girl out on a date and how to ask a girl I barely know out? Also, how do I know when to kiss her?