Jack is mortified after Grace catches him buying condoms in preparation for his big night with Missy (recurring guest star KERI LYNN PRATT). 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 (recurring guest star TOM CAVANAGH) slips back into his old habits, forcing Grace to make a difficult decision about her family. Also, Bobby tries to help Warren (recurring guest star DEAN COLLINS) woo a girl but is surprised when she declares she has feelings for Bobby.
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