While Bailey is totally unprepared for a coffeehouse waitress's freewheeling attitude about sex, Julia discovers that her deception forced Morgan to close his club and that his drinking problem has put him in no mood to forgive. Then, Claudia is upset when Ross suggests a new teacher, while Charlie discovers that Kirsten is planning on going home to her family. As Claudia learns just how much more demanding Gloria is than Ross, Bailey is invited over to Jill's house when her parents are out. But, before he can go to see what she has in store, he must first help Claudia when she gets her period for the first time. Meanwhile, after seeing a side of Morgan she never knew, Julia pours all his liquor down the drain hoping to stop his drinking.
At Jill's, Bailey's fumbling around makes clear that it's his first time. And, after learning that her sister Meg is serious about having her come back home, Charlie asks Kirsten to get married instead. After she accepts, he joins Bailey and Julia in offering some sage advice to Claudia about becoming a woman. But what they find is that she would rather stay a little girl. After telling Will that he's no-longer a virgin, Bailey voices doubts about Jill's uncommon willingness to have sex. He'd like a little romance and companionship, too. Meanwhile, Julia discovers Morgan's long history of alcoholism, while Charlie's proposal is undercut when Meg persuades Kirsten to reconsider.
When Jill begins to sense that he's losing interest, Bailey struggles to explain how he wants more than just sex. Claiming she isn't ready for a new teacher, Claudia convinces Ross to take her back for now, while Julia decides that Morgan will have to help himself before she can do anything to turn his life around. Dropping by the coffeehouse where she works, Bailey asks Jill out on a date, hoping they can back up to a point where he's more comfortable. Finally, Charlie's last ditch appeal convinces Kirsten to move in with the Salingers and try living together.
Directed by: Ellen Pressman
Written by: Ann Lewis Hamilton