My first proper date was sophomore year in high school when I got my license. I'd done stuff with girls before, but it always required getting a ride, other people being around, doing stupid things, etc...
I remember I really liked this girl and asked her if she wanted to hang out sometime. She said yes and I got her number. I called her a couple days later and asked her if she wanted to go bowling. Again, she said yes, so we went and got some dinner and then went bowling. It went pretty well. We ended up dating for a bit. I couldn't have asked for a first date to go any better.