Jesse is taken to a psychiatrist to find out why she isn't eating. Karen's firm is hired to oppose the building of Miles' building -- the one Rick is designing.

Jessie's glitter is missing, and Grace and Carla are the prime suspects. Rick discovers some unsettling news about both sides of his project with Miles. Evidence is discovered concerning Jessie's progress in therapy.

Lily and Rick begin their wedding plans and want Judy to help, but Judy seems hesitant. Jesse faints and falls in the girls' locker room. Grace learns of it and voices her concern to Judy. Judy tells Karen, who tells Jesse, and argument ensues. Dr. Rosenfeld tells Rick and Karen to put restrictions on Jesse's activities until she eats what Rick and Karen ask her to. Jesse, of course, doesn't like this either. Judy reveals to Jesse that she was bulimic when she was younger. Judy finally blurts out that she doesn't trust Rick enough to watch Lily get married to him. Karen makes the decision not to let Jesse go on the ski trip with her classmates. This makes Jesse even more upset. Judy and Rick settle, somewhat, their differences. Dr. Rosenfeld makes Karen realize that she can't control every possible aspect of her and Jesse's life. Lily and Judy make up, and Karen lets go enough to allow Jesse to go on the ski trip.

A boy in the play school play asks Jesse out. Grace is less than happy with the news, because she thought that the boy was flirting with her during rehearsal. Karen is upset that Rick didn't left her out of the loop on this. Les takes over a talk show after the host leaves following an argument between the two. He asks for Lily's opinion on a call (while on the air), which leads to her taking over the show that night, and a once-a-week gig after that. Rick and Lily argue about her discussing Jesse's ""date"" when it hasn't been decided if he'll let her go. Grace thinks about quitting the play (over her sorta-feelings for Tad and the whole Tad-Jesse thing), but that's not what she tells Mr. Dmitri. He convinces her to stay. Grace is irate that Lily offered to loan Jesse Lily's pearl necklace when she wouldn't let Grace borrow it earlier. Grace is starting to think that Lily likes her stepdaughter Jesse more than her. Karen accuses Lily of using Jesse's personal life for radio ""mat

Grace pursues her teacher and Jessie develops an attraction for her friend Katie.