Dear Miss Information,
I have this friend who I might like to date, but she's unbearably shy….How can I draw her out of her shell? I'm sure we'd both be happier that way. — Shy Times Two
Well, I know you'll be happier. She'll be doing all the work and taking all the risk by asking you out. I'm going to age myself about twenty years in two sentences, but, as my mom used to say:
What's the matter with you? You got a broken leg? YOU ask her out.