Guest Stars Anna Wheeler as Kylie Lafferty Savannah Basley as Grace Wilson Lara Jean Chorostecki as Candace Porter Brittany Drisdelle as Nisha Collins Christie Stewart as Mindy Palmer Carrie-Lynn Neales as Holly Preston Michael Worthman as Armando Melanie O'Brien as Date #1 Megan Kennedy as Date #2 Ebony Pharamond as Deirdre Joseph Cannata as Nate Abrams Kara O'Keefe as Date #3