Your story tells me it's your inner game that needs work.
Get some of Hypnotica's stuff and do the exercises. The football walk works best for me. I do it every night so I wake up feeling full of confidence. It seems like your inner game not just because of your story but because of how you wrote it. You keep saying you "might" do something or start something. You need to be more assertive man!
Kino is a major aspect of interacting with a girl. Without kino you'll end up in the LJBF zone and I don't think you want that. A lot of us make a big deal out of kino but it's really not. I used to be afraid to touch a girl
now I laugh at how I used to feel. You can start off kino by simply talking with your hands and being enthusiastic. When you're saying something interesting just touch her hand or shoulder or something. Trust me it's easy. You just need to get in the habit of talking with your hands. It's tough if you don't do it normally but it also makes you more interesting to talk to. I constantly have to remind myself to gesture because I'm not accustomed to it. Most of the time when I'm not gesturing etc I feel like the conversation is dragging along. Just get out there and touch them... 
I saw you said you haven't made girl 1 laugh yet...I suggest you get Cocky Comedy and other conversation skills by david deangelo. It's a great program. He goes into the social aspect of laughter. It tells you that laughter is more a indication of status etc. There's some good concepts there that will definitely help you out. Use a funny opinion opener until then. You can start of serious and tell them you have something serious you wanna get their opinion on. Really build up the tension. Pause a second or 2 then break the tension with a silly question like "do you stand by your microwave and stop it as soon as it hits zero in order to stop the beeping?" or "do you floss before or after you brush your teeth?" etc. Think of one and use it!
Let loose and enjoy life. You can be mature and still have fun. Do some fun stuff so you have something to talk about. Life is there for us to live it and enjoy it you just have to try. I know it's tough man but you can do it! Let me know how it goes.