|Season 2, Episode 2|
|Air date||November 1 2013|
|Written by||Jessica O'Toole & Amy Rardin|
|Directed by||Amy Heckerling|
"Win Some, Lose Some"
Carrie and Walt are faced with kicking out their new roommate when she makes herself too comfortable. Walt summons the courage to tell Bennet how he feels about him at his eighteenth birthday bash – at a VIP Z100 concert - but things go horribly awry before Bennet can respond. Samantha and Mouse meet, and Samantha wastes no time giving Mouse sex tips. Back in Castlebury, Sebastian and Maggie run into each other; and the evening doesn’t go exactly as planned when Tom invites girlfriend Deb to spend the weekend with him.
- 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
- Nadia Dajani as Deb