Guest Stars Jon Huertas as Miguel Rivas Lonnie Chavis as Young Randall Pearson Hannah Zeile as Young Kate (15) Sam Trammell as Ben Niles Fitch as Young Randall (15) Logan Shroyer as Young Kevin (15) Da'Vine Joy Randolph as Tanya Victoria Macabu as Young Kate Co Starring Eris Baker as Tess Pearson Faithe Herman as Annie Pearson Mackenzie Hancsicsak as Young Kate Pearson Parker Bates as Young Kevin Pearson Megan West as Heather Travis Guba as Stu Nikiva Dionne as Female Trader A.J. Rivera as Donny Watson Terryn Westbrook as Ashley Alexander Lewis as LA Waiter Clint Jordan as Kevin's Coach Andrew Adams as NY Waiter Hollie Shay as Hot Girl Fan Uncredited Seth Meyers as Himself