Guest Stars Miriam Flynn as Sister Helen Lisa Arch as Rebecca Sean Masterson as Tom Sheehan Emmett Shoemaker as Ryan Sheehan Co Starring Jarrett Lennon as Croyce Daniel Farber as Mitchell Jessica Stier as Ashley Vanessa Vander Pluym as Lydia Di Quon as Natalie Hira Ambrosino as Mrs. Pollack Iris Almario as Date #2 (Alice) Nicholl Hiren as Date #3 (Elanor) Chancellor Miller as Kid in the Crowd