Guest Stars Kate Owens as Sophie Hale Alyshia Ochse as Maisy Glendower Cassi Maddox as Young Kendra Rae Philips Brian Baumgartner as Colin Franklin Co Starring Zele Avradopoulos as Bridget Adena Brumer as Shannon Langston Kerman as Jesse Watson Jonathan Baron as Matt Adam Murray as Stranger Patrick Broderick as Speaking Portrait #1 Linda Copeland as Speaking Portrait #2 Frank Jennings as Speaking Portrait #4 Charles Fries IV as Speaking Portrait #3