The Carrie Diaries

Win Some, Lose Some

E1    Oct 25, 2013    42m    TV-14
Add Show to Watchlist
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.
Where to Watch Win Some, Lose Some
Cast of Win Some, Lose Some
  • AnnaSophia RobbCarrie Bradshaw
  • Austin ButlerSebastian Kydd
  • Ellen WongJill 'Mouse' Chen
  • Katie FindlayMaggie Landers
  • Stefania LaVie OwenDorrit Bradshaw
  • Brendan DoolingWalt Reynolds
  • Freema AgyemanLarissa Loughlin
  • Matt LetscherTom Bradshaw
  • Jake RobinsonBennet Wilcox
  • Lindsey GortSamantha Jones
  • Evan CrooksMiller

Take Plex everywhere

Watch free anytime, anywhere, on almost any device.
See the full list of supported devices