This is where most guys hit a wall. "Never leave a conversation because you've run out of things to talk about," Savoy says. At the very least, use something like, "that's just like when . . ." to keep things moving. If you're feeling confident, try the "cold read"—tell her something about herself based on her appearance or mannerisms. Point out her striking cheekbones or her cute laugh. Her reaction will open up a new avenue in the conversation.