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

Sam places his dream of committing to Judy and having a family squarely on the shoulders of his ten-year-old son. Meanwhile, Jake finally realizes his feelings for Tiffany and his new baby daughter.