Bart will be visited by many of his past girlfriends. Zooey Deschanel, Anne Hathaway, Sarah Silverman, Natalie Portman, and Sarah Michelle Gellar will guest star, reprising their roles as Mary Spuckler, Jenny, Nikki McKenna, Darcy, and Gina Vendetti.

Al Roker, Anne Hathaway, Don Pardo, Ken Burns, Kevin Michael Richardson, Maurice LaMarche, Natalie Portman, Sarah Michelle Gellar, Sarah Silverman, Zooey Deschanel