Chicago native Emily Jones (Autumn Reeser) loves her city, and has dedicated her career to coordinating its beloved Thanksgiving Day parade every year. This year, Emily is hoping for a memorable holiday and anticipating a long-awaited proposal from her long-distance boyfriend Brian (Ben Cotton). Then, the parade director hires a wealthy development consultant, Henry Williams (Antonio Cupo), to analyze the finances of the parade and increase profits.
Jess and David's wedding is here, but the O'Brien family still has a lot to face before the celebration. Abby and Evan get into an argument over his hotel, threatening the entire project.
Helen Bouchard starts the edits of Elizabeth's manuscript. When Lee gets injured, a newcomer's words of comfort cause Rosemary to reflect on what she wants in life.
A light snow falls as Cassie and Sam walk out of the bistro. When Sam called to tell her the news that Linda had gone back to New York, Cassie left John's faculty formal to make sure Sam was okay. Sam explained that before leaving, Linda made amends for the way she had treated Nick and he seems to be handling her leaving well. Sam then asks Cassie about her date with John, adding that it's nice of Cassie to fill in for John's girlfriend. Cassie hesitates before telling Sam that John and his girlfriend broke up. She then reveals that John was a bit of a player in college, with lots of girlfriends but none of them serious. It's also why he and Cassie have always been just friends. Sam chuckles and then suggests they need to celebrate. Sam then conjures an inspired idea and suggests that the location of their date be a surprise for Cassie.
