Julia Roberts (Mystic Pizza)
Kirsten Dunst (Bring It On)
Julia Stiles (A Guy Thing)
Maggie Gyllenhaal (The Dark Knight)
Ginnifer Goodwin (Walk The Line)
Dominic West (300)
Juliet Stevenson (Bend It Like Beckham)
Marica Gay Harden (Mystic River)
John Slattery (Iron Man 2)
Topher Grace (That 70s Show)
Kristen Connolly (The Cabin In The Woods)
Krysten Ritter (Jessica Jones)
Lily Rabe (The Undoing)
In 1953, Katherine Ann Watson (Julia Roberts), a 30-year-old graduate student in the department of Art History at Oakland State, takes a position teaching “History of Art” at Wellesley College, a conservative women’s private liberal arts college in Massachusetts, because she wants to make a difference and influence the next generation of women. At her first class, Katherine discovers that her students have already memorized the entire textbook syllabus, so she uses the classes to introduce them to Modern Art and encourages discussion about topics such as what makes good art and what the Mona Lisa’s smile means. This brings her into conflict with the college president (Marian Seldes), who warns she must stick to the syllabus if she wants to keep her job. Katherine comes to know her students and seeks to inspire them to achieve more than marriage to eligible young men.
Betty Warren (Kirsten Dunst) is highly opinionated and outspokenly conservative like her mother, the head of the Alumnae Association. Betty doesn’t understand why Katherine is not married and insists that there is a universal standard for good art. She writes editorials for the college paper, exposing campus nurse Amanda Armstrong (Juliet Stevenson) as a supplier of contraception, which results in Amanda being fired; another editorial attacks Katherine for advocating that women should seek a career instead of being wives and mothers as intended. Betty can’t wait to marry Spencer (Jordan Bridges) as their parents have arranged and expects the traditional exemptions from attending class as a married woman: Katherine insists she will be marked on merit and attendance, resulting in more conflict.
Connie Baker (Ginnifer Goodwin) begins dating Betty’s cousin, Charlie (Ebon Moss-Bachrach) but Betty persuades her that he is only using her his parents have arranged for him to marry Deb MacIntyre. After a disastrous date, where Charlie and Connie very nearly cross paths with Deb’s parents on a weekend away at the shore, Connie ends the relationship, believing Betty’s story to be true. However, some weeks later, Connie and Charlie reconnect, with Charlie saying he has already decided for himself that he is not going to marry Deb, so he and Connie get back together. Joan Brandwyn (Julia Stiles) dreams of being a lawyer and has enrolled as pre-law, so Katherine encourages her to apply to Yale Law School, where she is accepted; Katherine is affronted when Joan’s fiancé Tommy (Topher Grace) comments Joan “will always have that”, intimating his own expectations of what his wife should be. Joan eventually elopes with Tommy, and professes to Katherine she is very happy—she had decided that what she wants most is to be a wife and mother after graduation and asks Katherine to respect her choice. Giselle Levy (Maggie Gyllenhaal) has liberal views and supports Katherine because she sees her as having chosen what she wants in her life and because she has often felt out of place at the school being Jewish among the mostly WASP student body. Her parents divorced after the war and her father left them for a new family. Giselle brazenly has affairs with a professor and a married man.
During “truth or consequences” in a secret society meeting, Katherine confides to the girls that she was engaged when she was younger, but that she and her fiancé were prevented from marrying by the war and their relationship fizzled out. Katherine declines a proposal from her California boyfriend (John Slattery) because she doesn’t love him enough and begins seeing the Wellesley Italian professor, Bill Dunbar (Dominic West). Bill is charming and full of stories about Europe and his heroic actions in Italy during the war. He has also had affairs with students (including Giselle), and Katherine makes him promise that it will never happen again. The relationship progresses but when Katherine learns that Bill spent the entire war at the Army Languages Center on Long Island, she decides to break up with him because he is not trustworthy. Bill responds that Katherine didn’t come to Wellesley to help the students find their way, but to help them find her way.
Within six months of the wedding Betty’s marriage falls apart as Spencer has an affair, hiding it from his wife by pretending to be away on business. Betty seeks refuge at her parents’ house but her mother turns her away, telling her that her home is with Spencer now. Betty lashes out at Giselle in rage and pain and then breaks down in tears while Giselle hugs her. Mrs Warren begs Betty to stay married to Spencer, saying that she should try for a year and that she must avoid a scandal. Betty shows her mother a picture of the Mona Lisa and asks if her smile means she is happy. She answers her own question: “Who cares, as long as she’s smiling?” and warns her mother that not everything is what it seems. At graduation, Betty begins to ask Katherine about apartments in Greenwich Village, New York, but their conversation is interrupted by Mrs. Warren. Betty tells her mother that she filed for divorce that same morning and she is going to room with Giselle. She tells Katherine that she is considering applying to Yale Law School.
Katherine’s course is highly popular, so the college invites her to return but with certain conditions: she must follow the syllabus, submit lesson plans for approval, keep a strictly professional relationship with all faculty members, and not talk to the girls about anything other than classes. Katherine decides to leave in order to explore Europe. In the final scene, Betty dedicates her last editorial to Katherine, claiming that her teacher is “an extraordinary woman who lived by example and compelled us all to see the world through new eyes.” As Katherine’s taxi speeds up, all her students follow on their bicycles and Betty is seen struggling to keep up with the taxi as a last effort to thank Katherine for changing her life.
This is a wonderful, highly enjoyable film in which the social mores and style of the nineteen fifties are well depicted