As the season begins, it's the summer of 1985 and 17-year-old Carrie Bradshaw (ANNASOPHIA ROBB) can call Manhattan home. She also meets a new friend: Samantha Jones (LINDSEY GORT).
Carrie and Walt are faced with kicking out their new roommate when she makes herself too comfortable. Walt summons the courage to tell Bennet (recurring guest star JAKE ROBINSON) how he feels about him at his 18th birthday bash - at a VIP concert for the radio station Z100 featuring indie rock band AMERICAN AUTHORS - but things go horribly awry before Bennet can respond. Samantha and Mouse meet, and Samantha wastes no time giving Mouse sex tips. Back in Castlebury, Sebastian and Maggie run into each other; and the evening doesn't go exactly as planned when Tom invites…
Larissa returns from her summer in Kyoto and insists on taking Carrie and Walt to a fabulous Japanese festival in the city, where Larissa meets Samantha, with an explosive result. Samantha seduces an acrobatic ninja. Back in Castlebury, Carrie's plans to remain zen backfire when she finds herself locked in a classroom alone with Sebastian. Mouse helps Maggie with her college applications, but Maggie is distracted when somebody from her past reappears. Meanwhile, Walt worries that his classmates will sense he is gay, and Harlan (guest star SCOTT COHEN) makes an offer …
Carrie spends an exciting day in the city with playwright Adam Weaver (recurring guest star CHRIS WOOD). Samantha, who booked a new job as a nude art model, takes matters into her own hands when she sees a student's painting she doesn't like. Sebastian finds support in surprising places when his mother (recurring guest star NOELLE BECK - Person of Interest, As the World Turns) announces she is marrying her tennis instructor boyfriend. Elsewhere, the attempts of Dorrit's boyfriend (recurring guest star EVAN CROOKS) to get closer to her backfire.
When Carrie struggles with writer's block, Weaver (recurring guest star CHRIS WOOD) tries to help but gets in the way. Maggie and Sebastian grow closer after learning some shocking news. When Bennet (recurring guest star JAKE ROBINSON) moves to a dangerous neighborhood, Walt takes drastic measures to keep himself safe, with both hilarious and heartfelt results. Meanwhile, Larissa and Samantha finally find some common ground: sex. Recurring guest star RJ BROWN appears as West.
Carrie is shocked when she reads a nasty rumor about her in a New York City gossip rag, but Samantha has a plan to set the record straight. Walt steps in when Bennet (recurring guest star JAKE ROBINSON) feels taken advantage of at Interview. Mouse, worried that she and boyfriend West (recurring guest star RJ BROWN) are stuck in a rut, does something very risquÃ©. Meanwhile, when Maggie experiences a medical emergency, Sebastian is forced to reach out to the one person who can help. Plus, Samantha and Carrie attend the exclusive “Paris Party.” Recurring guest star …
Carrie is delighted when she gets the chance to interview the CEO of Bongo Jeans - but the pressure is on when Larissa tells Carrie that this is her last chance to land a piece in Interview magazine. Mouse gets some news that drives an unexpected wedge between her and West, and Sebastian's father delivers other news that could forever change Sebastian and Carrie's relationship. Elsewhere, Walt finds a surprising father figure in Tom, and Maggie tries to muster the courage to tell her dad the truth about the last few months.
Larissa gives Carrie some harsh advice about her relationship with Sebastian. When Harlan (recurring guest star SCOTT COHEN) asks Tom to work overnight on a top-secret case, Dorrit decides to throw an impromptu get-together, which quickly spirals out of control. Meanwhile, Mouse and Donna get surprisingly close and Sebastian makes a hasty decision after another fight with his parents.
Walt and Bennet (recurring guest star JAKE ROBINSON) get some devastating news that forever changes their future. Sebastian gets an exciting work opportunity, causing him to bail on Carrie on Valentine's Day, much to her chagrin. When Maggie accidentally enlists in the army, a surprising duo comes to her rescue. Elsewhere, Tom uses some reverse psychology to encourage Dorrit to start dating again.
When Bennet (recurring guest star JAKE ROBINSON) starts slacking at work, Carrie tries to cover for him. However, when Larissa finds out, things backfire big time for both of them. Samantha makes an uncharacteristic decision about her latest fling. Sebastian's father (recurring guest star TERRY SERPICO) asks him for a favor that could change Sebastian's future forever. Meanwhile, Tom is hoodwinked by another lawyer - a beautiful lawyer - when negotiating a deal, and is advised by the person he least expects.
Carrie, Mouse, Maggie and Walt decide to go together to their senior prom at The Waldorf Astoria as a final hurrah. Larissa offers Carrie an opportunity that makes her rethink her plans for the next year. Mouse learns a secret about Donna LaDonna that could threaten her reign as queen bee. Meanwhile, Sebastian hides a big decision from Carrie.
Things grow increasingly tense between Carrie and Tom. When Larissa drops an unexpected bomb on Carrie, Sebastian decides he, too, needs to come clean about something. Maggie turns to Walt when she thinks Pete is cheating on her, but gets the surprise of her life. Mouse and West find themselves in a sticky situation. Elsewhere, Samantha considers leaving the city, and Larissa's wedding to Harlan is out of this world.