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.