Monica can't sleep because of her break up with Richard. She finds his hair in the drain and thinks about keeping it because it's all she has left of him, but then she realizes it's gross drain hair and doesn't. Then she finds one of his cigars on the balcony and lights it just to smell it. Later she has a package at the post office to find it's the civil war tapes she ordered for Richard because he loved the Civil War. Phoebe tries to do aromatherapy on her so she'll go to sleep but it doesn't work. At the end of the episode her dad comes over for a little "Monica-cuddle". He tells her that Richard is doing terrible, even worse than when he got a divorce this makes Monica feel a little better and she finally goes to sleep.
Meanwhile, Ross reveals his sex fantasy about Prince Leah. Ross finds out that Rachel told Phoebe about his fantasy and gets upset. She tells him that all women do that and that he should too. So he and Chandler try to share with each other. Instead Chandler tells Ross about picturing his mom during sex and scares Ross. At the end of the episode Rachel dresses up like Princess Leah, instead of seeing Rachel, Ross sees his mother, just like Chandler told him about. This ruins the mood for him and Rachel stands there with a confused look on her face.