Guest Stars Erin Way as Erin Cherry Jones as Holly Maddox Yahya Abdul-Mateen II as Omar Co Starring Jordana Blake as Hannah Philip Craig as Maintenance Van Driver Joanna Douglas as Heather Amanda Barker as Tricia Michala Brasseur as Caitlyn Isaiah Rockcliffe as Adam Michelle Hospedales as Holly's Friend #3 Asia Rempel as Young June Janelle Heron as Econowife Vas Saranga as Kyle Jessica Greenberg as Holly's Friend #4 Katie Messina as Carol Alex Harrouch as Young Driver Trevor Hayes as Pilot Catherine McNally as Sarah