Continuity mistake: In the confrontation scene where all of Mary's admirers are forcing her to choose between them, Woogie is sat on the couch with a pile of Mary's shoes. Every time the camera shoots back to him, you will notice that the position of the shoes changes each time. This is also mentioned by the directors on the DVD commentary.
There's Something About Mary (1998)
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Directed by: Peter Farrelly, Bobby Farrelly
Starring: Ben Stiller, Cameron Diaz, Matt Dillon, Lee Evans, Chris Elliott
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Trivia: Dropping Ted while he was on the stretcher was not intended, it accidentally collapsed. When it did, the Farrelly brothers called cut to make sure Ben Stiller was alright, and then just left it in.
Question: Healy tries to impress Mary by pretending to be an architect, drugging the dog, getting new teeth, liking the same movies, and by saying he works with handicapped children. Why then would he call them "r***rds" and say he keeps one in a cage and puts him on a leash like a dog?! Wouldn't he think this would piss Mary off? I never understood that scene and why he would say this.
Chosen answer: Apparently he didn't consider that - either he's just being an idiot or he's trying to make an extremely ill-considered joke. Either way, that's a character mistake, not a movie mistake.
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Answer: Because he is ignorant and doesn't know anything about disabled people, he actually doesn't realise what he is saying is offensive.