The kids question Cate's motives when they return from their summer getaways and discover that she has bought a new bed and changed her hairstyle. Meanwhile, after traveling through Europe over the summer, Kerry met and had a fling with a boy - which leaves Bridget jealous and Kerry wondering what to do about boyfriend Kyle; new high school Student Body President Bridget is convinced even further that life is a popularity contest after taking a trip to Washington, DC over the summer; and after a depressed Jim fails to win back the affections of his wife in Florida, Rory attempts to help him quit smoking -- which is complicated by Jim's discovery that C.J. was responsible for their irreconciliation.

Kerry is livid when Bridget unintentionally makes a mockery out of her art project at the mall. But she quickly forgets about Bridget when fellow artist and young hottie Tyler asks her out on a date. However Tyler's intentions may not be completely genuine. Meanwhile, while C.J. finds himself striking out at speed dating, Jim discovers that he's a hit with the ladies-which further humiliates his socially inept grandson.