I suspect that what is going to happen is that he is going to end up driving to a Nazi bunker with a cleaner, in a TVR Tuscan he found abandoned in a field along with a can of Red Bull that fell from orbit. Or something.
Reminds me of my youth being terrified of asking. I manned up, asked a hot German Girl out i worked with, got a date, 3 months and some amazing shagging, whole thing was doomed and mistake but was fun for 3 months.