Win Some, Lose Some
Season 2, Episode 1
2x01 - Win Some Lose Some - Infobox
Air date October 25 2013
Written by Amy B. Harris
Directed by Andy Wolk
Episode Guide
"Kiss Yesterday Goodbye"
"Express Yourself"

Win Some, Lose Some is the 1st episode of Season Two and the 14th episode of The Carrie Diaries overall and the Second Season's Premiere.


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 best friends in 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.




Guest StarringEdit




Start a Discussion Discussions about Win Some, Lose Some

  • Mr Big

    4 messages
    • Oooh fascinating.
    • Except for the fact that Mr. Big is more than 10 years older than Carrie so that can't be him.