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.

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 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.