Special Guest Stars Josh Peck as Drew Guest Stars Ashley Reyes as Hannah Aby James as Rachel Daniel Augustin as Ian Co Starring Hudson Brooks as Young Jesse Kennedy Bryan as Young Sophie Jesten Mariconda as Delivery Person Brian Carpenter as Rupert Cooper Mothersbaugh as Todd Amari McCoy as Mariah Matt Linton as Partygoer Elizabeth Caro as Olivia De Marco Olivier Paris as Brendan