The trip to the Newman family ranch for the wedding runs aground thanks to years of family tension between Bobby, Jack and their father.
In the season finale, Jack and Bobby discover that Grace plans to visit their father, Juan (LOU DIAMOND PHILLIPS - "La Bamba," "Hollywood Homicide"), in a Texas prison. Bobby insists on joining her, and along with Jack they embark on a spontaneous road trip, during which Grace is forced to reveal the shocking reason their father is in prison. The future reveals Jack's heartbreaking fate and details Bobby's unlikely road to the presidency. And, for the first time, the voice of President McCallister (Academy Award winner TIM ROBBINS - "Mystic River") is heard. Author GORE VIDAL appears as the Host of the McCallister documentary, and producer NORMAN LEAR ("All in the Family") portrays the elderly Peter Benedict, Bobby's future father-in-law.
To protect Marcus, Jack tells the police that he was driving the car the night Missy died. The guilt becomes too much for Marcus, and he confesses to his dad, who immediately calls Grace. A surprising ally comes to Jack's aid after Grace demands that he tell the police what really happened. Meanwhile, the group's sadness turns to outrage after Reverend Belknap (recurring guest star ED BEGLEY, JR.) delivers a shocking eulogy at his daughter's funeral. Also, Bobby feels betrayed when Warren's (recurring guest star DEAN COLLINS) family plans to move to Chicago.
Jack, Courtney, Marcus, Missy (recurring guest star KERI LYNN PRATT) and Randy (recurring guest star CAM GIGANDET) leave a boring school dance and drive to an after-hours party, but a deadly car accident prevents them from making it to their destination. Meanwhile, much to Bobby's dismay, Grace chaperones Bobby's school field trip, which proves to be a hurtful and eye-opening experience for Grace.
Missy (recurring guest star KERI LYNN PRATT) reveals a secret to Jack that could change their lives forever. As a result of her actions, Missy is kicked out of her home and turns to Grace for support and guidance. Meanwhile, Bobby surprises Grace by telling her that he would like to be baptized and tries to convince Peter to be his godfather.
Jack finds out that Bobby has secretly decided to try out for the track team, and Jack instantly shows his disapproval. Later, Jack realizes that his relationship with Katie (recurring guest star KATE MARA) isn't what he thought it was and is shocked to find out that Courtney and Marcus may have feelings for each other. Meanwhile, Grace's excitement to be the opening speaker at an event for her mentor turns to disappointment when she is asked not to speak due to her scandalous relationship with Tom (recurring guest star BRADLEY COOPER--not appearing in this episode).
Jack and Katie's (recurring guest star KATE MARA) relationship progresses, while Courtney's comes to a screeching halt after Jack discovers Nate (recurring guest star MIKE ERWIN) is cheating on her with another girl. When Bobby is required to do a family history project for class, he goes through his mother's closet for clues and discovers a letter that reveals the real reason his father left. Meanwhile, Grace is shocked to learn that her affair with Tom (recurring guest star BRADLEY COOPER) has cost her more then she had bargained for. NEIL PATRICK HARRIS ("Doogie Howser, M.D.") guest stars as Preston Phelps, a graduate student in the year 2045.
Peter is forced to take action after learning about the relationship between Grace and Tom (recurring guest star BRADLEY COOPER). Meanwhile, Bobby and Warren (recurring guest star DEAN COLLINS) decide to make some cash by doing yard work in their neighborhood and are shocked when they find Jack's wallet in a neighbor's garage. After learning that his wallet was discovered and realizing who attacked him, Jack and Marcus take matters into their own hands.
Grace and Tom's (recurring guest star BRADLEY COOPER) relationship is exposed when a fellow professor catches them kissing in Grace's office. Later in the evening, Peter turns to Grace for advice when he finds out Courtney is having sex with her boyfriend. Meanwhile, Jack's relationship with classmate Katie (recurring guest star KATE MARA) progresses. And in an effort to become popular at school, Bobby and Warren (recurring guest star DEAN COLLINS) decide to have a sleepover and come up with a shocking idea to make the evening memorable.
Jack catches Grace and Tom (recurring guest star BRADLEY COOPER) 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.
Bobby becomes suspicious of Grace's relationship with Tom (recurring guest star BRADLEY COOPER) after Tom coincidentally shows up during a camping trip. While Jack and Missy's (recurring guest star KERI LYNN PRATT) relationship seems to be coming to an end, Courtney's dating life is heating up with college freshman Nate (recurring guest star MIKE ERWIN). The future reveals that President McCallister, despite the risks involved, supports space travel to the planet Mars.
Jack tries to resume a sense of normalcy after a brutal attack but finds that the injury may keep him from returning to his old life. Grace is blackmailed by a student who caught her leaving Tom's (recurring guest star BRADLEY COOPER) room. And Courtney meets a new guy, Nate Edmonds (recurring guest star MIKE ERWIN), who captures her interest. The future reveals President McCallister's unique actions after a horrific bombing in Chicago.
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.
After the suicide of a friend, Jack is haunted by the thought that he should have done more to help. Meanwhile, Grace's warm, intelligent, gay younger brother, Jimmy (recurring guest star TOM CAVANAGH - "Ed"), makes a surprise visit for Thanksgiving. Grace is thrilled that he has returned, but her feelings change after he lands in jail on drug charges.
Grace promises to be on her best behavior when she and Jack go to Missy's (recurring guest star KERI LYNN PRATT) house for dinner but loses her temper after Missy's father, Reverend Belknap (recurring guest star ED BEGLEY, JR.), attacks her ideals. Upset by the event, Grace is comforted by Tom (recurring guest star BRADLEY COOPER), and the two share a romantic moment. Meanwhile, Bobby intentionally loses chess games to Peter in order to spend more time with him. And Courtney uses Marcus to retaliate against Jack.
Heartbroken after his relationship with Dex (recurring guest star JEANETTE BROX) ends, Bobby decides to retaliate against Jack when he learns his brother is responsible for their breakup. Bobby's actions cause embarrassment and anger between Jack, Missy (recurring guest star KERI LYNN PRATT) and Courtney, resulting in a feud between the brothers. Meanwhile, Grace and her teaching assistant, Tom Wexler Graham (recurring guest star BRADLEY COOPER - "Alias"), sneak away from the campus election-night party to smoke marijuana, but the transgression proves to be a terrible mistake for Grace and her family. The future reveals that in 2040, McCallister wins the election by only a few votes.
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