Guest Stars Yamaneika Saunders as Maya Sas Goldberg as Jess Arielle Siegel as Jen Gary Gulman as Shlomo Lily Fisher as Young Ann Cole Escola as Cole David Byrne as Dr. B Anjelah Johnson-Reyes as Kylie Mendes Dan Thompson as Tim Voight Co Starring Woody Fu as Bryan Daniel Powell as Jeff Emma Kantor as Young Jess Camiel Warren-Taylor as Young Maya Thomas Place as TBD Getchie Argetsinger as Helen Julia Tolchin as Young Jen Marco Canora as Himself Ansley Moncoeur as Ansley Luca R Stagnitta as Jason Joseph DiStefano as Rob Bob Roseman as TBD