Guest Stars Milana Vayntrub as Sloane Sandburg Janet Montgomery as Olivia Maine Ryan Michelle Bathe as Yvette Natalia Cigliuti as Josie Woods Co Starring Eris Baker as Tess Pearson Faithe Herman as Annie Pearson Lonnie Chavis as Young Randall Pearson Parker Bates as Young Kevin Pearson Mackenzie Hancsicsak as Young Kate Pearson Ava DeVoe as Samantha Caspian Diament as Young Prince Grace Hosman as Vicky Geraldine Uy as Casting Director Laura Wernette as Neighbor Lady Ozzie Rodriguez as Tony Meyer Patrice Marjorie Melaku as Passerby Uncredited John Rubinstein as Ron Schiller Wesley Sellick as Sean Patrick