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| Julia Roberts | Katherine Watson |
| Kirsten Dunst | Betty Warren |
| Julia Stiles | Joan Brandwyn |
| Maggie Gyllenhaal | Giselle Levy |
| Juliet Stevenson | Amanda Armstrong |
| Dominic West | Bill Dunbar |
| Ginnifer Goodwin | Connie Baker |
| Topher Grace | Tommy Donegal |
| John Slattery | Paul Moore |
| Marcia Gay Harden | Nancy Abbey |
| Jordan Bridges | Spencer Jones |
| Marian Seldes | President Jocelyn Carr |
| Donna Mitchell | Mrs. Warren |
| Terence Rigby | Dr. Edward Staunton |
| Laura Allen | Susan Delacorte |
Katherine Watson is a recent UCLA graduate hired to teach art history at the prestigious all-female Wellesley College, in 1953. Determined to confront the outdated mores of society and the institution that embraces them, Katherine inspires her traditional students including Betty and Joan to challenge the lives they are expected to lead.
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