Season 1: Episode 07: The One With The Blackout
There is a blackout in New York City and Chandler gets locked in an ATM vestibule with a gorgeous woman (JILL GOODACRE). As hard as he tries to be cool, all the wrong words (and gum) come out. Meanwhile, the rest of the gang converges on Monica's apartment and passes the time playing Monopoly, telling scary stories, and talking about sex. In the midst of their conversations, Ross realizes that he is definitely in the "friend zone" with Rachel -- a terrible place to be, since he was aiming for the "dating zone." Just as Ross decides he is going to go for it with Rachel, a fellow apartment building dweller, Paolo, enters their blackout proceedings and, as the lights come on, Paolo and Rachel are found kissing.