Bobby joins the "challenge program" at school and learns a powerful lesson. Meanwhile, Grace is startled by news that Bobby's new teacher gives her regarding Jack. Also, the flash-forward segments reveal how a surprising ally helps President McCallister out at a critical moment in his political career.

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.

Jack walks in on Grace and Tom in a compromising situation and tells Grace he disapproves of her romance. Meanwhile, Bobby convinces Grace to allow him to attend an overnight hunting trip with Peter, which proves to be an eye-opening experience for Bobby.

After getting into a big argument at the not-so-exciting school dance, Jack, Courtney, Marcus, Missy and Randy decide to drive to an after-party, but a deadly car accident prevents them from making it to their destination. Meanwhile, Grace agrees to chaperone Bobby's school field trip, much to Bobby's dismay, which proves to be a hurtful and eye-opening experience for Grace.