Teddy is excited when the school produces her play and she wants Charlie to be cast as the princess. Bob loses a lot of weight and gets carried away with his makeover. Gabe must do a report on an old person.

Teddy struggles with applications for college and she dreams that she is in different times in the past. Gabe faces his old teacher. Bob gets an old rock look.

Ten years in the future, 14 year-old Charlie watches a video diary that Teddy made about a fight she had with Gabe, in hopes that it will guide her through her fight with an 11 year-old Toby.

Ivy tricks Teddy into joining her family trip to Las Vegas. Gabe is secretly playing league baseball because he doesn't want his mother to embarrass him. Bert and Mrs. Dobbs announce their marriage and want to have the wedding at the Duncan house.