It's the fall of 1953 and Katherine Watson (JULIA ROBERTS) has left California and boyfriend Paul Moore (JOHN SLATTERY) for the New England campus of Wellesley College where she's to teach art history. She ends up being housemates with Nancy Abbey (MARCIA GAY HARDEN), the old-fashioned poise and elocution instructor, and meets Amanda Armstrong (JULIET STEVENSON), the school nurse whose lesbian lover has recently died.
Katherine has high hopes for teaching the best and brightest young women in the country, but knows of Wellesley's reputation for being the most conservative college around. Even so, she's shocked to learn that the various students - including Elizabeth "Betty" Warren (KIRSTEN DUNST), Joan Brandwyn (JULIA STILES) and Connie Baker (GINNIFER GOODWIN) - are basically wiling away their time until they get married and become wives and mothers to the likes of "catches" Tommy Donegal (TOPHER GRACE) and Spencer Jones (JORDAN BRIDGES).
Only the slightly bohemian Giselle Levy (MAGGIE GYLLENHAAL) seems to buck the trend, but she's interested in continuing her love affair with Italian professor Bill Dunbar (DOMINIC WEST) who's now set his sights on Katherine instead.
While dealing with that, Katherine also decides to chuck the class syllabus when she learns that her students are incredibly book smart but have no idea how to think outside the box. That obviously leads to strife with the college administrators who don't like her bending the rules as well as Betty who sets out to destroy her career, just like she did with Amanda. From that point on, Katherine tries to get her students to see the possibilities in their lives beyond serving their future husbands, all while dealing with her own personal life.