Grace's warm, intelligent, gay younger brother makes a surprise visit to the McCallister home for Thanksgiving. Grace is thrilled that he has returned but her feelings change after he lands in jail on drug charges. Meanwhile, Jack feels responsible for a friend's suicide.

Jack is mortified after Grace catches him buying condoms in preparation for his big night with Missy. Trying to be supportive of his actions, Grace insists that Jack talk to her about sex and questions him about whether he is sure Missy is the right girl. Meanwhile, Jimmy slips back into his old habits, forcing Grace to make a difficult decision about her family. Also, Bobby tries to help Warren win over his crush Deena but is surprised when she declares she has feelings for Bobby.