|Photo Credit: Patrick Harbron/The CW|
In "Win Some, Lose Some," after Carrie's (AnnaSophia Robb) boyfriend Sebastian (Austin Butler) and best friend Maggie (Katie Findlay) betrayed her last season, Carrie is determined to make the most of her summer, living with Walt (Brendan Dooling) in Manhattan - and all the grit and glamour it has to offer - even agreeing to a night on the town with Donna LaDonna (Chloe Bridges).
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 (Lindsey Gort).
Back in Castlebury, Mouse (Ellen Wong) shuts out Maggie when she sees her working at the country club, and Dorrit (Stefania Owen) has her own problems to contend with when Tom (Matt Letscher) finds out about her boyfriend Miller (guest star Evan Crooks).
Check out a sneak peek video below:
RJ Brown also guest stars. Andy Wolk directed the episode written by Amy B. Harris.