|Win Some, Lose Some|
|Season 2, Episode 1|
|Air date||October 25 2013|
|Written by||Amy B. Harris|
|Directed by||Andy Wolk|
"Kiss Yesterday Goodbye"
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.
- AnnaSophia Robb as Carrie Bradshaw
- Austin Butler as Sebastian Kydd
- Ellen Wong as Jill "The Mouse" Chen
- Katie Findlay as Maggie
- Stefania LaVie Owen as Dorrit Bradshaw
- Brendan Dooling as Walt Reynolds
- Chloe Bridges as Donna LaDonna
- Lindsey Gort as Samantha Jones
- Matt Letscher as Tom Bradshaw