History YMMV / TheresSomethingAboutMary

* Tucker dropping his keys and awkwardly trying to pick them up despite his handicap is awkward to watch. Having it happen again mere seconds later merits a chuckle. And then we find out "Tucker" was never disabled to begin with, which makes the whole struggle earlier look postively hilarious!

* CrossesTheLineTwice: Dom works at a law firm. When Ted shows up at his place of business, we see he's working on a presentation called "Bus Crash - 12 Kids Killed; What Does This Cost ''Us''?".

*** When Warren is first introduced, a pair of teens start
mocking him, then decide to pull a prank at his expense, exploiting his naivety by convincing him to ask a woman if she's seen his "wiener" instead of his baseball; while the instigating characters are never seen again and [[KarmaHoudini thus seem to get away with it]], they're not shown in a sympathetic light, and the scene is ultimately played for drama, as Ted steps in to defend Warren from the girl's angry boyfriend despite having never met him at this point.

mocking him, then decide to pull a prank at his expense, exploiting his naivety by convincing him to ask a woman if she's seen his "wiener" instead of his baseball; while the instigating characters are never seen again and [[KarmaHoudini thus seem to get away with it][, they're not shown in a sympathetic light, and the scene is ultimately played for drama, as Ted steps in to defend Warren from the girl's angry boyfriend despite having never met him at this point.

*** When Warren is first introduced, a pair of teens decide to pull a prank at his expense, exploiting his naivety by convincing him to ask a woman if she's seen his "wiener" instead of his baseball; while the instigating characters are never seen again and thus seem to get away with it, they're not treated sympathetically, and the scene is ultimately played for drama as Ted steps in to defend Warren from the girl's angry boyfriend despite having never met him at this point.

* NightmareFuel: The fate of Sully in the extended version. [[spoiler:He gets eaten by his pet boa constrictor, Bill]].

* TearJerker: Near the end there is a scene where he thinks he's blew it with Mary, and walks away sobbing loudly while being tormented by memories of all the good times he spent with Mary. [[spoiler: Fortunately she picks him after all.]]

* TheWoobie: Ted, especially during the zipper scene and towards the end of the film.

* UnintentionalPeriodPiece: Nowadays, Ted could just use social media to find out about Mary.

** When Warren is first introduced, a pair of kids decide to pull a prank at his expense, exploiting his naivety by convincing him to ask a woman if she's seen his "wiener" instead of his baseball; while the instigating characters are never seen again and thus seem to get away with it, they're not treated sympathetically, and the scene is ultimately played for drama as Ted steps in to defend Warren from the girl's angry boyfriend despite having never met him at this point.

* HarsherInHindsight: Brett Favre had a wholesome image at the time and makes the "perfect boyfriend" image make sense. However shortly after the film was released it was revealed that he had a serious problem with painkillers and alcohol that also led to a lot of serious family problems. A silver lining to Favre's issues though was that it did bring to light many of the problems professional football players face and the fact that they are in almost constant pain due to all the injuries they suffer. Despite their issues Favre is still with his wife (whom he was married to at the time of filming as well).
** Now a double whammy after allegations arose that Favre siphoned away money marked for state welfare programs for speaking appearances and to build a volleyball center at his daughter's alma mater.

* ValuesResonance: Mary rightfully calls out Pat for using ableist slurs such as "retard".

** Now a double whammy after allegations arose that Favre siphoned money marked for state welfare programs for speaking appearances and to build a volleyball center at his daughter's alma mater.

** Now a double whammy after allegations arose that Favre siphoned money marked for state welfare programs for speaking appearances and to build a volleyball stadium at his daughter's alma mater.

* HarsherInHindsight: Brett Favre had a wholesome image at the time and makes the "perfect boyfriend" image make sense. However shortly after the film was released it was revealed that he had a serious problem with painkillers and alcohol that also led to a lot of serious family problems. A silver lining to Favre's issues though was that it did bring to light many of the problems professional football players face and the fact that they are in almost constant pain due to all the injuries they suffer. Despite their issues Favre is still with his wife (whom he was married to at the time of filming as well). Now a double whammy after allegations arose that Favre siphoned money marked for state welfare programs for speaking appearances and to build a volleyball stadium at his daughter's alma mater.

* HarsherInHindsight: Brett Favre had a wholesome image at the time and makes the "perfect boyfriend" image make sense. However shortly after the film was released it was revealed that he had a serious problem with painkillers and alcohol that also led to a lot of serious family problems. A silver lining to Favre's issues though was that it did bring to light many of the problems professional football players face and the fact that they are in almost constant pain due to all the injuries they suffer. Despite their issues Favre is still with his wife (whom he was married to at the time of filming as well).

* ValuesResonance: Mary rightfully calls out Sully for using ableist slurs such as "retarded".

* AwardSnub: W. Earl Brown’s portrayal of Warren is one of the most accurate depictions of a person with a mild intellectual disability ever put on film.
* 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.
* FridgeLogic: Dom told Ted to have ADateWithRosiePalms before his date with Mary because he wanted to sabotage him by making him act un-masculine and platonic while on the date.
* HarsherInHindsight: Brett Favre had a wholesome image at the time and makes the “perfect boyfriend” image make sense. However shortly after the film was released it was revealed that he had a serious problem with painkillers and alcohol that also led to a lot of serious family problems. A silver lining to Favre’s issues though was that it did bring to light many of the problems professional football players face and the fact that they are in almost constant pain due to all the injuries they suffer. Despite their issues Favre is still with his wife (whom he was married to at the time of filming as well).

* PlayingAgainstType: Matt Dillon had always been known for playing tough guys and rebellious youths in dramas. In this comedy film he’s a slimy private investigator.

* WhatAnIdiot: 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?
** One possible explanation could be a case of GoodCannotComprehendEvil; Mary's so nice herself that she can't imagine a friend of hers doing that to her.