Factual error: A hard pack of Winston cigarettes is shown, but these were not available in 1953.

Factual error: When Julia Roberts and her roommate are in their living room and "I Love Lucy" comes on the TV, the opening theme song is accompanied by the traditional heart with "I Love Lucy" written on it. However, this movie takes place in 1953-1954, and that opening for the show wasn't used until the show was put in syndication many years later. During the show's primary run, cartoon characters of Lucy and Ricky opened the show.

Factual error: When the Wellesley College boss dictates to her secretary the key letter offering Julia Roberts a new contract but with teaching/artistic conditions which lead to Ms Roberts leaving, the secretary uses Teeline shorthand. The film is set in 1953/54, Teeline was invented by one James Hill in 1968.

Continuity: When Julia Roberts is sitting on the couch with the male teacher, after he pours her a drink, they move the camera and show her and her drink is almost empty and then they show him and the drink is almost full. They then repeat going from her with an almost empty glass to him with her glass almost full.

Audio problem: When Joanie and Tommy are eating dinner at Betty's home, there's a close-up profile shot of both Joanie and Tommy right before they kiss. Tommy says to Joanie, "Come here you," but his lips don't move.

Continuity: During an outdoor campus celebration, students dance around a May Pole, winding ribbons attached at the top around it. The ribbons are wrapped around the pole about five inches from the top. In the next shot, the ribbons are not yet wound around the pole as the girls circle it.

Other: Julia Roberts arrives at the school by train and the next scene is in cap and gown at the school opening ceremonies. The next scene shows her looking for lodging (wearing what she wore when she arrived by train). She then teaches her first class and is called in to see the president and goes to see her wearing something different. In the next scene she's back at the house where she's staying, wearing what she wore when she taught her first class. A plot hole continuity mistake?

Factual error: When we hear Doris Day singing "Secret Love" the record we see on the turntable has an RCA Victor label visible/readable. Doris Day songs were released on Columbia Records.

Factual error: The Waterford Castlemaine crystal pattern used for the etiquette lesson, and later in the house Julia Roberts lived in, did not exist in 1953. It was introduced in 1986.

Factual error: In the scene with the big band, the band is playing a tune in which the trumpets play the melody with a muted sound (this is kind of a "metallic" sound) yet the trumpeters don't have any mutes in their horns. They would have to be awfully good players to be able to make their trumpets sound like they are using metal mutes if there were none available. This is basically an impossibility.

Continuity: When Kirsten Dunst is getting married, and the bride and groom are having their photos taken, they talk about reading a poem, and Dunst hands over a piece of paper with the poem written down on it to her husband. When he takes it, he carries on holding her hand, but in the next shot, when a photo is taken, both characters' hands are down by their sides.

Continuity: In the scene where Dunbar gives Katherine her Christmas gift, the brick path that Katherine is walking on is wet and covered by ice and snow. When we have a closeup of Dunbar catching up with Katherine, the path is dry and has no snow or ice on it.