Guest Stars Tamara Tunie as Genevieve Victoria Clark as Diane Doyle Timothy Busfield as Ron Doyle Bryce Lorenzo as Izzy Molly Price as Judge Nicole Stephens Chris Conroy as Sam McCormick Co Starring Carme Boixadera as Kim Phoebe Dunn as Debbie Goldman Jesse Sharp as Caitlin's Father Beth Dzuricky as Housekeeper Fahim Hamid as Amanda's Assistant Andrew Lee as Nick Kaylin Hedges as Caitlin