Guest Stars Vinny Thomas as Omar Guy Branum as Stewart Francesca Delbanco as Diane Rachel Rosenbloom as Jenna Lewis Co Starring Max Matenko as Simon Sophie Leonard as Frances Sophia Kopera as Maeve Ankur Bhatt as Albert Penelope Stoller as Gemma Treisa Gary as Lawyer Sydney Ariel Flores as Kevin Cameron Bedford as Scooter Guy Jai Sahai as Johnny 66 Receptionist Frederica Stoller as Freddie Lydia Stoller as Lydia Gabby West as Neighbor Mom