Go out with him to the mall, and each go up to at least 5 girls and do these purposeful blowouts
"Hey, I'm not hitting on you or anything, but, will you be my girlfriend?"
"Hey, I'm not hitting on you or anything, but, can I get your number?"
Ask them directions to places and try to keep the conversation going whilst ONLY looking directly at their tits
Start talking to them nervously, and then try and ask for the number, but then drop your phone and a bunch of condoms out of your pocket and try and keep her there whilst picking them up
Ask them if they know where you can get a chlamydia test around here. Then proceed to ask them on a date.
- The point is to go in and realise the humour and fun behind getting blown out, and just revelling in the social awkwardness until it doesn't matter any more. After you have fun with these, opening normally is EASY!
p.s. I was a virgin at 19 too, it's nothing to be ashamed of.