Special Guest Stars Eion Bailey as Ray Guest Stars Erik Stocklin as Perry Whitley Sofia Vassilieva as Dierdre Andrew Walker as Coach Baker Lauren Bowles as Monica Grant Cole Bernstein as Jenny Kline Sterling Beaumon as Ian Hemingway Chloe Lanier as Sage Caitlin Carver as Alexis Peter Coventry Smith as Emmet Beaudry Austin Lyon as Tripp Buckley Sampson as Ian's Mom