Continuity: When Trip passes out at the Wordfest, and he wakes up with Sarah standing over him, watch her hands. Every time they switch shots, her hands switch back and forth between holding a cigarette and a box of cigarettes, to her simply having her hands at her sides.

Revealing: Michael Douglas pulls up to the curb to park his car. When he opens his door, it hits a fire hydrant, which moves! This is very easy to spot.

Continuity: In the scene where James Leer (Tobey Maguire) is getting dressed in Crabapple's room, we at first see James wearing just a pair of white underwear. The scene cuts away from him for a couple of seconds, and then cuts to him again, only this time he is wearing black pants. He couldn't possibly have gotten dressed that quickly.

Continuity: When James washes a codeine pill down with liquor he spits it at Tripp's chest. In two successive shots you see first liquor spraying at Tripp, then a sole pill flying at him, but liquor neither in the air nor on his coat.

Continuity: When Tripp meets Crabtree and his transvestite friend at the airport you see a lady in a black leather coat walking right behind them. Then they meet and exchange pleasantries, and when they move on the same lady is walking by in the same direction.

Continuity: When James takes a second try to get the pill down the liquor bottle is fuller than when he tries first.

Factual error: In the film we can see the jacket that Marilyn Monroe was wearing the day she married Joe DiMaggio, only the colour is wrong. We are shown a dark black jacket, though it actually was a brown one.

Continuity: When Tripp and Crabtree arrive at the Gaskells' house there is no snow. A little while later he goes out to get some fresh air, and everything is covered with a thick layer of snow, although it is snowing only lightly.

Revealing: When Tripp talks to James in the Gaskells' garden it is snowing quite a lot in the distance, but only very little at the place where they are standing.

Continuity: After Tripp and James break into Emily's parents' house James pours himself a glass of whiskey. When he leans back the glass is fuller than before.

Continuity: At the welcoming party Gaskell talks to Antonia. The dog comes and starts sniffing at her. When the camera angle changes the dog is sniffing at Gaskell.

Continuity: When Tripp, Crabtree, and Antonia arrive at the Gaskells' home Sara comes down the hallway with an almost empty wine glass. While they are talking she holds the glass in the right hand. Then her dog comes to attack Tripp, and when she grabs him at the collar the glass is suddenly in her left hand, and has changed to an almost full champagne glass.

Plot hole: In the beginning of the film, when Trip introduces Hannah in a voice-over, he says that she is always "compulsively clad in red cowboy boots. I had in fact never once seen her without them." If Hannah was simply just one of his students, this statement would be true, but since Hannah rents a room off him, there would be occasions when Hannah would not be wearing her boots at all. When Trip asks Hannah if he can borrow her car, for example.