After Carrie’s boyfriend Sebastian and best friend Maggie betrayed her last season, Carrie is determined to make the most of her summer, living with Walt in Manhattan – and all the grit and glamour it has to offer – even agreeing to a night on the town with Donna LaDonna. But when Donna shows up with Sebastian, Carrie decides to go out on her own, and by a series of surprising events meets one of the greatest loves of her life, Samantha Jones. Back in Castlebury, Mouse shuts out Maggie when she sees her working at the country club, and Dorrit has her own problems to contend with when Tom finds out about her boyfriend Miller.
Carrie and Walt are faced with kicking out their new roommate when she makes herself too comfortable. Walt summons the courage to tell Bennet how he feels about him at his eighteenth birthday bash – at a VIP Z100 concert – 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 girlfriend Deb to spend the weekend with him.
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 makes an offer Tom can’t refuse.
Carrie pitches Larissa a profile on New York wunderkind playwright Adam Weaver, but when he proves a difficult, yet fascinating, interview, Carrie’s job is on the line. Bennet’s rules in his relationship with Walt force Walt to acknowledge his real feelings. Carrie and Dorrit are surprised to find a common enemy in Tom’s girlfriend Deb’s son Dylan. Meanwhile, Sebastian seeks comfort in the arms of someone new.
When Sebastian learns that his mother is getting remarried, he asks for Carrie's dad to make sure she is legally protected. Carrie is furious when she discovers that Weaver has secretly read her journal. Mouse volunteers to help with the Homecoming float, but tries to distance herself when West wins Homecoming King. Samantha finds herself a place to live and another unusual job. Meanwhile, Dorrit begins to feel smothered by Miller, especially when he befriends her dad, and Donna LaDonna gives Dorrit some wise advice.
When Carrie struggles with writer’s block, Weaver tries to help but gets in the way. Maggie and Sebastian grow closer after learning some shocking news. When Bennet 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.
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 feels taken advantage of at Interview. Mouse, worried that she and boyfriend West are stuck in a rut, does something very risqué. Meanwhile, when Maggie experiences a medical emergency, Sebastian is forced to reach out to the one person who can help.
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 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 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 starts slacking at work, Carrie tries to cover for him. However, when Larissa finds out, things backfire big time for them both. Samantha makes an uncharacteristic decision about her latest fling. Sebastian’s father asks him for a favor that could change Sebastian’s future forever. Meanwhile, Tom is hoodwinked by another – beautiful – lawyer when negotiating a deal, and is advised by the person he least expects.
Carrie, Mouse, Maggie, and Walt decide to go to their senior prom – at The Waldorf Astoria – together for 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.
Recently, life hasn't been smooth sailing for 16-year-old Carrie Bradshaw – her mother just passed away, her rebellious younger sister Dorritt is acting out, and their father Tom is struggling to raise two teenage daughters alone. As Carrie begins the first day of her junior year, she can’t help but feel as though all eyes are on her, and a pity party from rival Donna LaDonna doesn't help the situation. Even when surrounded by her group of friends, Mouse, Maggie and Walt, Carrie feels as though her life should be heading in a different direction. The arrival of new guy Sebastian Kydd brings Carrie some excitement, but it isn't until she accepts an internship at a Manhattan law firm that things begin to fall into place. In the city, Carrie meets Larissa Loughlin, a free-spirited, outgoing style editor at Interview magazine, who introduces her to a world she’s only dreamt of.
New couple Carrie and Sebastian can't seem to catch a break. Between being grounded and rival Donna's sneaky attempts to break them apart, Carrie worries Sebastian will lose interest in her. Desperate for some alone time with him, Carrie must lie to her father and bail on plans with her sister Doritt Maggie's obsession with having sex drives a wedge between her and Walt Meanwhile, Larissa wants to do a photo shoot with Carrie's purse for Interview magazine forcing Carrie to scramble to make it work.
After Tom forbids Carrie to see Sebastian again, Carrie snoops through Tom's work files and uncovers some alarming information about Sebastian's past. Carrie decides to confront Sebastian about what she's discovered and is shocked by his reaction. Maggie deals with her breakup with Walt in the only way she knows how and finds some solace from Dorrit Meanwhile, Larissa takes Carrie, Mouse and Seth to an outrageous performance art club in New York City, which leaves them all feeling self-conscious.
When Carrie is invited to a Halloween party in the city by Larissa, she decides to invite Walt to go with her to keep her company. It doesn’t take long before the night goes awry and Carrie is forced to babysit Larissa, who has clearly taken too many drugs. Walt finds himself in an uncomfortable position after a party guest gets a little too close for comfort. Elsewhere, Maggie convinces Mouse to go with her to Sebastian’s Halloween party at the diner to help keep tabs on him. After Doritt’s attempt to sneak out of the house is thwarted, she discovers hanging out with her father isn’t so bad.
Carrie runs into an old friend at her internship and gets invited to his mother's dinner soiree in Manhattan, but her feelings for Sebastian get in her way, until she see him with another girl. Mouse is excited about getting back together with Seth, but her worries about being bad at sex drive her to ask Walt for help. In order to hang on to a favorite spot at the diner, Maggie takes on Donna LaDonna and her friends. Meanwhile, Tom loses his wedding ring, which makes him realize that Harlan might be right about starting to date again.
Carrie gets in way over her head when she tries to cook the perfect Thanksgiving dinner for her family, her new boyfriend George and his dad Harlan, so she enlists Mouse's help. Tom is oblivious to the chaos going on in the kitchen, while Dorrit finds a new way to torture Carrie. Maggie is excited to have Thanksgiving with Walt's family, but when the topic of college comes up she realizes that she hasn't put much thought into her future. Elsewhere, Sebastian learns that his mother decided to fly out of town with her boyfriend, leaving him to fend for himself on Thanksgiving.
Impressed with Carrie's creative prowess, Larissa offers her an internship at Interview, but Carrie is torn about whether she should take it. Carrie invites George to the school dance, but when she suggests they leave the dance early, George gets the wrong idea about her intentions. Dorrit, who used to go to the Nutcracker ballet with her mother every year, reluctantly agrees to go with Tom, but he has a hard time filling his wife's shoes. Mouse gets a B+ on an exam and blames it on her relationship with Seth Meanwhile, Donna LaDonna catches Maggie cheating on Walt and blackmails her into keeping Carrie away from Sebastian.
Carrie is thrilled when the junior-senior lock-in provides the perfect cover for a night out in Manhattan with Larissa and her Interview co-workers - until a surprising encounter turns her night upside down. Maggie and Mouse confront Sebastian about his feelings for Carrie and tell him he better make a grand gesture if he stands any chance of winning her back. Harlan finally convinces Tom to go on a double date, with surprising results. Meanwhile, Maggie tries to find the courage to tell Walt about Simon before Donna LaDonna does.
When Dorrit goes missing under Carrie's watch, Carrie lashes out at Sebastian, the one person who can help her find Dorrit. Mouse butts heads with West, a popular jock who, much to her chagrin, stole her spot as number one in the class. Walt surprises himself when he confides in someone completely unexpected. Meanwhile, Tom finds himself in uncharted territory when it comes to women and turns to Larissa for advice.
On her seventeenth birthday, Carrie torn between an opportunity to mingle with New York’s literati and spending time with her friends and Sebastian. Mouse goes to extensive lengths to impress a Harvard alum who has her eyes set on West, with hilarious results. Walt starts taking responsibility for his previous actions. Elsewhere, Dorrit’s search for the perfect gift for Carrie lands her in a sticky situation with romantic possibilities.
Carrie jumps at the chance to a take on a fabulous new identity as Larissa, but gets more than she bargained for when Larissa’s hijinks catch up with her. After a whirlwind day in Manhattan, Walt is forced to face the feelings he is desperately trying to hide. Sebastian and Maggie agree to keep a secret from Carrie. Mouse takes a page from Donna LaDonna’s playbook. Meanwhile, Tom decides to take a meditation class, but finds himself surprisingly tense after a run-in with another attendee.
When Carrie inadvertently complicates things with Sebastian, she tries to fix it by taking him to Madonna's "The Virgin Tour" launch party - but in her quest for the perfect night, only makes things worse. Despite Mouse's best efforts to avoid West, she can't seem to deny the romantic sparks flying between them. Dorrit turns to Donna LaDonna for advice about her budding love life. Meanwhile, Tom has an awkward encounter when he spends the night somewhere new.
Carrie is happy going to her junior prom, but when hidden secrets are revealed plans begin to change. Dorrit is determined to take her relationship with Miller to the next level, but things hit a bump along the way. For the first time in her life, Mouse decides to defy her parents to date whom she wants. Tom begins to struggle with sneaking around, especially when he thinks someone might be on to him. Elsewhere, Larissa makes Carrie and Walt an enticing offer.