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Cady Huffman as Divorcing Mom Reathel Bean as Doorman Alison Wright as Bridget Rose Gonzalez as South American Nanny Charlie Hewson as JoJo Nate Corddry as Calvin Joanna Heimbold as Glamour Mom Matilda Szydagis as Polish Nanny James Urbaniak as Educational Consultant Kimmy Suzuki as Flying Nanny (uncredited) John Henry Cox as Dean Sakina Jaffrey as Sima Julie White as Jane Gould Roy William Gardner as Golfer (uncredited) Brendan Griffin as Kenny Aaron Staton as John David Boston as Parent at College Graduation (uncredited) Alicia Keys as Lynette Chris Evans as Hayden “Harvard Hottie” Donna Murphy as Judy Braddock Nicholas Art as Grayer Stella Stark as Nanny (uncredited) Judith Roberts as Milicent Jodi Michelle Pynn as Screeching Lady Paul Giamatti as Mr. X Kaitlin Hopkins as Bitsy Isabel Keating as Paranoid Mom Georgina Chapman as TriBeCa Fashionista Laura Linney as Mrs. X Patrick Heusinger as Carter Scarlett Johansson as Annie Braddock Heather Simms as Murnel Stephen O'Reilly as Reggie Eli Harris as Lewis (uncredited) Mike Rad as Dude Allison Sarofim as Eating Disorder Mom Nina Garbiras as Miss Chicago Brande Roderick as Tanya Tina Benko as Shopaholic Mom Ilana Levine as Whiny Mom Kevin Kraft as Pierrot #1 Marla Sucharetza as Charity Mom

Bob Weinstein Executive Producer Terry Stacey Director of Photography Catherine George Assistant Costume Designer Jill Brown Stunts Shari Springer Berman Screenplay, Director Harvey Weinstein Executive Producer Jeffrey Lee Gibson Stunts Stephen A. Pope Stunts Blaise Corrigan Stunts Mark Suozzo Original Music Composer, Music Programmer, Orchestrator, Music Producer, Conductor Michael Wilkinson Costume Design Richard N. Gladstein Producer Robert Pulcini Editor, Screenplay, Director Patricia Birch Choreographer Luke Owen Camera Loader Matthew Landon Co-Producer Samantha MacIvor Stunts Heba Thorisdottir Makeup Artist