Friends: Season 1, Episode 22

1 - 22: The One With the Ick Factor

Monica has a new boyfriend, Ethan. But after they sleep together for the first time, Ethan reveals he is a high school student. Meanwhile, Phoebe becomes Chandler's secretary and hits it off with his colleagues. But she discovers no-one at his office likes him because of his promotion, so Chandler sets out to prove that he has not changed since becoming "the boss", whilst Rachel begins having erotic dreams about Joey and Chandler, making Ross envious.