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.