* FridgeHorror: It is ''very'' likely the entire reason Woogie not only befriended Ted but became his best friend was to eventually use him to get to Mary. Not only that, but he ''always'' resented him because Ted (in Woogie's mind) stole Mary from him.
** There is also the fact that he never loved his wife and kids.
* HilariousInHindsight: One of the cops who interrogates Ted after he's arrested at the gay orgy at the rest stop is named [[Series/LawAndOrderSpecialVictimsUnit Detective Stabler]]. Even more hilariously, he's ''not'' the RabidCop of the pair.
* {{Too Dumb to Live}}: The only reason that Mary broke up with Brett was because she received a letter from Tucker informing her of how he felt about Mary's brother. She then gets the similar treatment regarding Pat Healy when Tucker mentions Healy's fake past. And then ''again'' when he sends her a letter about Ted. (Though it later turned out to be Woogie's doing). How did she not think Tucker or ''someone'' was sabotaging her relationships out of jealousy or because they were in love with her and trying to remove the hypotenuses?
* MarySue: Possibly lampshaded with Mary, [[MeaningfulName as her name is literally Mary.]] She is always portrayed in a positive light and throughout the film multiple guys lie and cheat their way in other to have some form of a chance of dating her.
* NightmareFuel: The fate of Sully in the extended version.
* OneSceneWonder: Keith David as Mary's stepfather. And the police officer who's going to break Ted. Harland Williams as the serial killer who's going to sell seven minute abs.
* TheWoobie: Ted, especially during the zipper scene and towards the end of the film.
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