Life hasn't been smooth sailing for 16-year-old Carrie Bradshaw: her mother just passed away, her younger sister is acting out, and their dad is struggling to raise two teenage daughters alone. The arrival of sexy new guy Sebastian Kydd brings Carrie some excitement.
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.
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.
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.
Carrie runs into an old friend and gets invited to his mother's dinner soiree in Manhattan, but her feelings for Sebastian get in her way. Mouse is excited about getting back together with Seth, but her worries about being bad at sex lead her to ask Walt for help.
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.
Carrie invites George to the school dance, but when she suggests they leave the dance early, George gets the wrong idea about her intentions. 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.
When Dorrit goes missing under Carrie's watch, Carrie lashes out at Sebastian, the one person who can help her find her sister. Mouse butts heads with West, a popular jock who, much to her chagrin, stole her spot as number one in the class.
On her 17th birthday, Carrie is 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.
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.
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 it only makes things worse.
Carrie is happy going to her junior prom, but when hidden secrets are revealed plans begin to change. For the first time in her life, Mouse decides to defy her parents to date whom she wants. Elsewhere, Larissa makes Carrie and Walt an enticing offer.
Carrie is determined to make the most of her summer in Manhattan and all the grit and glamour it has to offer. She agrees to a night on the town and, by a series of surprising events, meets one of the greatest loves of her life - her lifelong friend Samantha Jones.
Carrie and Walt are faced with kicking out their new roommate when she makes herself too comfortable. Samantha and Mouse meet, and Samantha wastes no time giving Mouse sex tips. Back in Castlebury, Sebastian and Maggie run into each other.
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.
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. Meanwhile, Sebastian seeks comfort in the arms of someone new.
Carrie spends an exciting day in the city with playwright Adam Weaver. 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.
When Carrie struggles with writer's block, Weaver tries to help but gets in the way. Maggie and Sebastian grow closer; Walt takes drastic measures to keep Bennet safe, with both hilarious and heartfelt results; Larissa and Samantha finally find some common ground: sex.
Carrie is shocked when she reads a nasty rumour about her in a New York City gossip rag, but Samantha has a plan to set the record straight. Plus, Samantha and Carrie attend the exclusive "Paris Party" .
Carrie is delighted when she gets the chance to interview the CEO of Bongo Jeans, but the pressure is on as it's her last chance to land a piece in Interview magazine. Plus, Sebastian's father delivers news that could forever change Sebastian and Carrie's relationship.
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.
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. Tom uses some reverse psychology to encourage Dorrit to start dating again.
When Bennet starts slacking at work, Carrie tries to cover for him. When Larissa finds out, things backfire big time for both of them. Samantha makes an uncharacteristic decision about her latest fling; Tom is hoodwinked by another lawyer when negotiating a deal.
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. Sebastian, meanwhile, 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. Elsewhere, Samantha considers leaving the city, and Larissa's wedding to Harlan is out of this world.