Carrie (AnnaSophia Robb) is thrilled when the junior-senior lock-in provides the perfect cover for a night out in Manhattan with Larissa (Freema Agyeman) and her Interview co-workers - until a surprising encounter turns her night upside down. Maggie (Katie Findlay) and Mouse (Ellen Wong) confront Sebastian (Austin Butler) about his feelings for Carrie and tell him he better make a grand gesture if he stands any chance of winning her back. Harlan (guest star Scott Cohen) finally convinces Tom (Matt Letscher) to go on a double date, with surprising results. Meanwhile, Maggie tries to find the courage to tell Walt (Brendan Dooling) about Simon (guest star Josh Salatin) before Donna LaDonna (Chloe Bridges) does.