Jack and Bobby McCallister are two brothers being raised in Hart, Missouri by their eccentric single mother Grace, a college professor. Grace's strong personality and beliefs are instilled in both of the boy's lives, leading one of which to become President of the United States. The Benedict family, Peter and his daughter Courtney, move to Hart, and they both have an impact on the McCallister's lives.
Grace, with the help of Bobby, organizes and leads a Democrat rally for the college students. Jack catches Grace smoking pot again, and becomes enraged. Meanwhile, Jack and Courtney's budding relationship continues to grow, and we see how President McCallister became affiliated with a surprising political party -- Republican.
While Grace is out of town for a faculty retreat, Jack plans a big party at the house. At school, Bobby learns a life lesson after he joins the "challange program". Meanwhile, Grace finds out that her graduate TA plagerized one of her papers, and is torn between how to approach the problem. Also, flash-forwarding to the McCallister presidency shows a critical move in the President's career.
Warren has to study for his upcoming Bar Mitzvah and after Bobby helps him, he becomes interested in religion. Grace's class is boycotted after she insults an Arab-American student, then chastises her in front of the class. Later, Grace has to explain how she feels about religion to both Bobby and the Arab-American student. Meanwhile, Jack rejoins the track team as a replacement for Marcus.
Jack takes Courtney to a fundraiser put on by her father. The night leads to a surprise confession and a kiss. At school, Bobby has trouble with a bully, but soon finds a way to deal with him. Meanwhile, Grace invites a homeless man to stay at the McCallister's house until he finds something more permanent. In a flash-forward to the future, a secret about the future First Lady is revealed.
At the college, one of Grace's collegues is accused of sexual harassment. Grace defends him until new and startling evidence is uncovered. Bobby, after spending too much time with Dex, cheats on a test to bring his grades back up. Jack is surprised to find that Missy and Courtney have become friends.
Grace catches Dex and Bobby together, then teams up with Jack to get the two to break up. Courtney wants to date a frat boy, but Peter won't let her do so. In scenes from the future, we learn that President McCallister had problems controlling one of his sons, Jack, and the secret service.
Bobby finds out that Jack was behind his break up with Dex, and sets out to get even. Bobby's attempts to get even causes a rift between the two brothers. Meanwhile, Grace and Tom smoke pot together, which ends up to be a mistake. Later, the results of the 2004 election come in and scenes from the future reveal the outcome of the 2040 presidential election.
Grace attends dinner at Missy's house, despite Jack not wanting her to. As Jack predicted, Grace embarasses him after she loses her cool over the Reverend's political beliefs. Later, Grace and Tom share a romantic encounter. Meanwhile, Bobby starts spending more time with Peter by intentionally losing chess matches and flash-forwards to the future reveal how President McCallister used chess as a war strategy.
Jimmy, Grace's gay brother, visits the McCallisters for Thanksgiving. At first, everyone is happy about his visit, but their feelings soon change after he gets put in jail. Meanwhile, Matt, one of Jack's teammates, develops a crush on him. Jack's reaction to the crush sends Matt into a deep depression, and ends up committing suicide. Jack becomes distraught when he feels responsible.
Grace runs into Jack at the supermarket while he's in line to buy condoms. Grace tries to be supportive and talk to him about whether or not Missy is the one he wants to be with, but Jack is reluctant to talk with her. Meanwhile, Grace has to give some tough love to Jimmy when he returns to his old ways. Bobby tries to get Warren and Deena together, but Warren is hurt when she tells him that she likes Bobby.
Jack tries to go back to his normal life after his attack, but is having trouble adjusting to his injuries. Grace gets caught leaving Tom's apartment by one of her students, who uses what she saw to blackmail Grace into getting a high grade. Meanwhile, Courtney tries to get close to a college boy, but is let down when he doesn't have the same feelings. Lastly, scenes from the future reveal how President McCallister dealt with a devistating bombing in Chicago.
Bobby begins to catch on to Grace and Tom's relationship after he goes on a camping trip with Grace and him. Jack and Missy's relationship struggles when Missy begins to focus her attention on Randy instead of Jack. Courtney's relationship with Nate continues to progress. Meanwhile, Jack meets Katie at his doctor's office and an unlikely friendship emerges. Future scenes show how President McCallister backs space travel to Mars.
Jack walks in on Tom and Grace, leading Jack to tell Grace what he thinks of the relationship. Bobby talks Grace into letting him go on a hunting trip with Peter, but the experience wasn't what Bobby had imagined it to be. Meanwhile, Courtney and Nate take their relationship to the next level, and Jack begins to hang out with Katie while he deals with Courtney and Randy's new relationship.
Grace and Tom's relationship is exposed when a collegue catches them kissing in Grace's office. Jack and Katie continue to get closer. Bobby and Warren have a sleepover in an attempt to become popular at school. But when a severe snow storm hits Hart, Tom, Warren, Bobby, and the other boys at the sleepover are snowed in, and across town, Jack, Courtney, Missy and Katie are also trapped together. There, the foursome plays truth or dare, and Jack winds up kissing Courtney on a dare. Grace is trapped in Peter's office, and Peter asks Grace for advice about Courtney and Nate's relationship.
Peter takes action against Grace and Tom's relationship, leading Grace to face the Ethics Committee. Bobby and Warren land a job cleaning out Mrs. Sorensen's garage, and they find evidence that connects Mrs. Sorensen's grandson to Jack's attack. Jack and Marcus try to take action against Jack's attacker, but each one of their plans falls through.
For a school assignment, Bobby has to research his family's history. Bobby's research lead to more questions than answers about his past. Jack and Katie's budding relationship continues to progress, but Courtney and Nate's ends after Jack sees Nate cheating. Grace and Tom continue to deal with the aftermath of their affair.
Grace has to adjust to having a new TA, now that Tom is no longer around. Grace meets up with an old collegue, but is scared that he'll find out about her affair with Tom. Jack disapproves with Bobby wanting to join the track team. Meanwhile, Jack learns that his relationship with Katie wasn't what he thought it was, and is suprised to learn that Marcus and Courtney may have feelings for each other. Lastly, Missy talks to Jack and reveals some startling news.
Missy's suspicions are confirmed when the school nurse tells Missy she's pregnant. Jack and Missy tell their parents and they come together to discuss what actions should be taken. However, things don't go well and Missy is thrown out of her house. Grace agrees to take Missy to have a procedure done. Meanwhile, Bobby decides he wants to be baptized, but can't until a family member agrees to accompany him.
After an argument at a school dance, Randy, Missy, Courtney, and Jack decide to go to an after-party. However, they never reach their destination due to a deadly car accident, where one of the four is killed. Meanwhile, Grace chaperones Bobby's field trip, much to his embarassment. Scenes from the future reveal that one of President McCallister's children was killed in a drunk driving accident and the situation around the accident.
The aftermath of the accident begins to set in. Missy's parents are distraught after learning of her death, and Jack lies to the police about who was driving in order to protect Marcus. However, Marcus is racked with guilt and eventually confesses to his father, who is torn about what to do. Meanwhile, Warren learns that he's moving and Bobby has a hard time saying goodbye.
In an episode that details the future, a voice over explains the brother's futures. Jack fights in the War of Americas and is badly injured. He later becomes a public defender, a Congressman, but his life is tragically cut short buy a drug addict. Bobby takes over Jack's seat in congress. The episode ties in the boy's visit to with their father, Juan, in prison where Jack decides to meet him. Juan explains his reason for leaving and how he was wrongly convicted. This drives Jack to be a public defender. Lastly, Jack reveals his feelings to Courtney and Tom returns to see Grace.