Jack and Bobby McCallister, two smart siblings with lots of promise, live under the domineering watch of their single mother, professor Grace McCallister in Hart, Missouri.
Jack fights with Grace over her continued use of marijuana, but she disregards his ultimatum to stop, with negative consequences to follow. Meanwhile, Bobby attempts to smooth things over for Jack in school and with Courtney, but his efforts also take a disastrous path. It is revealed as to how the President eventually chose his political party affiliation.
Bobby's thinking is irrevocably changed when he joins up with the "challenge program" in school. His teacher, meanwhile, has some revealing information about Jack to impart to Grace. It is also learned how President McCallister is later given a helping hand by an unlikely ally.
Grace must reassess her own teaching methods when an Arab-American student comes to her claiming her lectures are reflective of her skepticism towards religion. The effect is a series of walkouts from Grace's classes on the part of campus religious groups. Meanwhile, while assisting his friend Warren with Barmitzvah preparation, Bobby becomes curious about religion and demands to know from his mother why he was never allowed to go to church.
In the future, a troubling secret about the First Lady comes to light. In the present, Courtney takes Jack up on his offer to escort her to her father's fundraising affair, which leads to a moment of honesty and a kiss. Meanwhile, tension is abound in the McCallister house when Grace offers a few days of shelter to a homeless man.
Grace is shocked to learn from Benedict that a colleague has been accused of sexual harassment by a student. After coming to his defense, however, she begins to think her colleague may not be so innocent after new evidence surfaces.
Bobby's quiet relationship with Dex is revealed when Grace catches the pair kissing in her study. Grace and Jack are soon trying to personally intervene after Grace is unable to coax Bobby into putting a stop to the relationship.
After breaking up with Dex, Bobby is devastated, but his emotions turn to rage and revenge when he learns that Jack is behind the breakup, and his response to the situation causes a torrent of problems between Jack, Missy, and Courtney.
Grace and Matt go to a family dinner at Missy's house, but Grace's attempts to keep her composure go awry when the Reverend begins to critique her beliefs. Grace's vulnerable admission to Tom about the evening ends with an intimate moment. Meanwhile, Bobby tries to spend more quality time with Peter by intentionally losing a game of chess to him, while Marcus becomes a part of Courtney's plan to get even with Jack.
Grace's much-beloved gay younger brother pops in for a Thanksgiving visit, but the good vibes are short-lived after he is arrested on drug charges. Meanwhile, when a friend of Jack's commits suicide, Jack begins to harbor feelings of guilt and wonder if perhaps he played a part in the terrible event.
Grace inadvertently spots a humiliated Jack buying condoms for an upcoming night with Missy. In an attempt to make him feel less awkward, she offers to tell him anything he wants to know about sex and tries to make sure Missy is the girl he really wants to be with.
Jack finds himself unable to get back to his normal life after the recovery from the horrific attack proves more difficult than imagined. Grace is the victim of a blackmail plot by a student who witnessed her exit from Tom's room. Meanwhile, Courtney slowly becomes enamored of a new guy, and the future shows the president dealing with bomb crisis in Chicago.
Tom conveniently happens to show up at a camping trip Bobby and Grace are on, prompting Bobby to air his suspicions and resentment. Meanwhile, Courtney's relationship with Nate begins to grow just as Jack and Missy's begins to fizzle. Also, the future finds President McCallister showing support for the travel to and exploration of Mars.
Jack expresses his discontent over Grace's relationship with Tom after he accidentally walks in on them in an intimate occasion. Meanwhile, Bobby coaxes Grace's permission for what will be a fateful overnight hunting excursion with John.
Grace and Tom's secret relationship is discovered when another professor walks in on their kiss in Grace's office. Peter asks Grace about what to do when he learns that Courtney is sleeping with Nate. Jack's relationship with Katie, meanwhile, intensifies, while Bobby and Warren have a sleepover and try to turn it into a cool night that will up their popularity in school.
Peter decides to go an extreme measure after he finds out about Grace's relationship with Tom. Meanwhile, Bobby and Warren decide to earn some extra money doing yard work for neighborhood homeowners, but when Bobby finds Jack's wallet, missing since his attack, in one of the house's garages, Jack is alerted and, together with Marcus, plans a way to pay back his now-revealed assailant.
Jack and Katie's relationship begins to head into deeper territory, but when the two discover Courtney's boyfriend Nate on a date with another girl and Jack spills the beans, Courtney decides to stop her relationship with Nate dead in its tracks.
Jack is instantly critical of Bobby's decision to try out for the track team. He also becomes disillusioned when he realizes that Katie may not be the girl for him, but turns to Courtney only to find that she and Marcus may have developed an attraction to one another.
Jack is stunned when Missy tells him a secret that could have dire effects on both of their futures. When the secret gets her kicked out of her house, she looks to Grace for some advice and direction. Meanwhile, Bobby tells Grace he wants to be baptized and attempts to get Peter to agree to be his godfather.
After a dispute during a school dance causes Jack, Courtney, Marcus, Missy, and Randy to decide to head off to an after-party, the group gets into a fatal car accident which stops them in their tracks along the way. Meanwhile, Grace gets a quick and stinging education in what means to try and play chaperone for one of Bobby's class field trips.
Jack tries to shield Marcus from the legal ramifications of the car accident by assuming the responsibility, but when Marcus' guilt begins to overwhelm him, he tells his father the truth, who then must square the truth with Grace.
Jack and Bobby learn that Grace plans to go to Texas to visit their father, Juan, in prison and insist that they be allowed to come along. During an impromptu road trip, Grace must finally open up to her children about why their father went to prison.