Guest Stars Lennon Stella as Maddie Conrad Maisy Stella as Daphne Conrad 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 J.D. Souther as Watty White David Clayton Rogers as Jason Erin McCarley as Adria Marcus Lewis as Joe the Bouncer