Grace and Jack's temperamental mother/son relationship takes a dangerous toll on Bobby as he gets caught in their rival forces, prompting a major change in the McCallister household. The arrival of a new college president, Peter Benedict, and his beautiful daughter, Courtney, makes an impression on the McCallisters that lasts a lifetime.

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.