Recientemente, la vida no ha sido fácil para Carrie Bradshaw, de 16 años: su madre acaba de fallecer, su rebelde hermana menor Dorritt se está portando mal y su padre, Tom, está luchando por criar solo a dos hijas adolescentes. Cuando Carrie comienza el primer día de su tercer año, no puede evitar sentir que todos los ojos están puestos en ella, y una fiesta de lástima por parte de su rival Donna LaDonna no ayuda a mejorar la situación. Incluso cuando está rodeada de su grupo de amigos, Mouse, Maggie y Walt, Carrie siente que su vida debería tomar una dirección diferente. La llegada del nuevo chico Sebastian Kydd le trae algo de emoción a Carrie, pero no es hasta que acepta una pasantía en un bufete de abogados de Manhattan que las cosas empiezan a encajar. En la ciudad, Carrie conoce a Larissa Loughlin, una editora de estilo extrovertida y de espíritu libre en la revista Interview, quien le presenta un mundo con el que sólo había soñado.

La nueva pareja Carrie y Sebastian parece no poder tomar un descanso. Entre el castigo y los astutos intentos de su rival Donna de separarlos, a Carrie le preocupa que Sebastian pierda interés en ella. Desesperada por pasar un tiempo a solas con él, Carrie debe mentirle a su padre y abandonar sus planes con su hermana Doritt. La obsesión de Maggie por tener relaciones sexuales abre una brecha entre ella y Walt. Mientras tanto, Larissa quiere hacer una sesión de fotos con el bolso de Carrie para la revista Interview. Carrie se esforzará para que funcione.

Después de que Tom le prohíbe a Carrie volver a ver a Sebastian, Carrie husmea en los archivos de trabajo de Tom y descubre información alarmante sobre el pasado de Sebastian. Carrie decide confrontar a Sebastian sobre lo que descubrió y queda sorprendida por su reacción. Maggie lidia con su ruptura con Walt de la única manera que sabe y encuentra algo de consuelo en Dorrit. Mientras tanto, Larissa lleva a Carrie, Mouse y Seth a un escandaloso club de artes escénicas en la ciudad de Nueva York, lo que los deja a todos sintiéndose cohibidos.

Cuando Larissa invita a Carrie a una fiesta de Halloween en la ciudad, ella decide invitar a Walt a ir con ella para hacerle compañía. No pasa mucho tiempo antes de que la noche se tuerza y ​​Carrie se vea obligada a cuidar a Larissa, quien claramente ha consumido demasiadas drogas. Walt se encuentra en una posición incómoda después de que un invitado a la fiesta se acerca demasiado para sentirse cómodo. En otra parte, Maggie convence a Mouse para que la acompañe a la fiesta de Halloween de Sebastian en el restaurante para ayudar a vigilarlo. Después de que se frustra el intento de Doritt de escaparse de la casa, descubre que salir con su padre no es tan malo.

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.

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.