Molly Ringwald Anne Juergens Actor Shailene Woodley Amy Juergens Actor Mark Derwin George Juergens Actor India Eisley Ashley Juergens Actor Daren Kagasoff Ricky Underwood Actor Francia Raisa Adrian Lee Actor Megan Park Grace Bowman Actor Greg Finley Jack Pappas Actor Ken Baumann Ben Boykewich Actor Jennifer Coolidge Guest Star Josie Bissett Guest Star Anne Ramsay Guest Star Camille Winbush Guest Star DeVaughn Nixon Guest Star Valerie Tian Guest Star Katelyn Tarver Guest Star Ana Lucasey Guest Star Mindy Cohn Guest Star Larry Clarke Guest Star Johnny Dark Guest Star Brenda Hampton Executive Producer