Nah, you were looking for something relatively organic to happen. I'm reasonably confident that homeboy was answering the question with some variant of "I'm crying because I'm ugly and unlovable" and closing the deal with "like someone as beautiful as you could never be attracted to a guy like me"
What you needed was a giant bolt and nut. Buddy of mine would take a thick 5" bolt & nut to parties,sidle up to a hottie and start screwing the nut onto the bolt in her peripheral. She'd notice, turn and ask "what you got there?". "It's a big bolt I found" then they're talking, then they're leaving!