Guest Stars Vinny Thomas as Omar Guy Branum as Stewart Janet Varney as Vanessa Emily Kimball as Peyton Francesca Delbanco as Diane Sarah Yarkin as Maddie Co Starring Max Matenko as Simon Sophie Leonard as Frances Sophia Kopera as Maeve Janine Poreba as Office Mom Jane Courtney Lauren Cummings as Riley Gigi Bermingham as Marla Ambrit Millhouse as Morning Pick Up Mom Laura Thomas Nowell as Alan Monica Loomba as Assistant