Guest Stars Maren Heary as Dolly Holloway Frank Deal as Gary Levine Megan Sikora as Michelle Kessler Paris Remillard as Hunter Abbott Kimberly Quinn as Holly Faitelson Shiloh Fernandez as Tom Devins Co Starring Ali Marsh as Blair Salz Erin Neufer as Emily J.C. Montgomery as Principal Krappel Shunori Ramanathan as Stacey Nancy Lemenager as Eleanor Elizabeth Inghram as Lindsay Stella Schnabel as Meditation Instructor Declan Fong as Hotel Restaurant Waiter Craig Beck as Bellhop