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.