Guest Stars Lennon Stella as Maddie Conrad Maisy Stella as Daphne Conrad Chris Carmack as Will Lexington David Alford as Bucky Dawes Kourtney Hansen as Emily Judith Hoag as Tandy Hampton Kimberly Williams-Paisley as Peggy Kenter Sylvia Jeffieres as Jolene Barnes Todd Truley as Marshall Evans Chloe Bennet as Hailey Susan Misner as Stacey Douglas Jay Hernandez as Dante Rivas