In “Win Some, Lose Some,” after Carrie’s boyfriend Sebastian (Austin Butler) and best friend Maggie (Katie Findlay) betrayed her last season, she 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. 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).
The Carrie Diaries Season 2 Premiere Promo
Posted to: The Carrie Diaries