* AudienceAlienatingPremise: The short version -- it's a family comedy about three 11-year-old boys who want to see a naked prostitute. Try selling that to a modern audience. The film also weaves in odd tonal moments like an 11-year old boy complaining that he's losing the "battle of the sexes" (leading him to seek out works like Magazine/{{Cosmopolitan}}, then hire a hooker, in an attempt to be "mature"), the third act playing heavily into the DamselInDistress trope by making V a brief hostage who has to be rescued and ferried by said group of pre-teen boys, or the comedy (yes, in a family friendly film) that's mined by V trying to... [[TheOldestProfession ply her trade]] in a small-town suburb where everyone knows each other.
* BileFascination: You'll be left pondering how such a premise tried to pass itself off as a family-friendly comedy.
* CrossesTheLineTwice: A sequence in the third act has Waltzer (having just escaped from a school gymnasium storage closet after being locked in by the boys when they rescue V) storms out into the school's parking lot and forcefully drags another hooker[=/=]TheInformant, Betty, to their car, claiming that she's "not worth a single bullet" while Betty tries to justify that she is. You read that right -- the BigBad is trying to convince himself ''not'' to shoot a hooker, while the hooker in question ''is trying to convince him to shoot her'' (albeit, in an inebriated state). This is PlayedForLaughs in a family-friendly film.
%% DesignatedHero: Neither the three boys nor V herself are that likable.
* {{Glurge}}:
-->'''V:''' There ''is'' a place you can touch on a woman that will make her go crazy.
-->'''Frank:''' Where?
-->'''V:''' Her heart.
** The entire film may count. [[AudienceAlienatingPremise The premise is disturbing enough]], but to make it a ''lighthearted family comedy?!''
* [[HoYay Les Yay]]: The girls are a little too into Frank's class presentation.
* MemeticMutation: "I'm going to the So'op."
* NoYay: The concept of a pre-teen boy who convinces a HookerWithAHeartOfGold to hide out in his treehouse, takes baths in his house when his father is out (and her being ''seemingly okay'' with him walking in on her mid-bath), the odd way she interacts with him (hugging him close at several points, in ways that are clearly set up as sex jokes) and ''dancing over him while wearing a short skirt'' when he's laying on the ground looking upwards at a school dance, in front of teachers, is likely to elicit this reaction from audiences.
* {{Squick}}: The film, as a whole, engages in moments that were barely (if at all) tolerated at the time it was made, and are far less forgiving in the modern age.
** The entire concept of a group of pre-teens paying a hooker to flash them. To note -- the actual production of the scene ''barely'' skirted legality between Griffith and the children, as she wore Post-It notes over her breasts to comply with decency requirements involving minors on-set.
** The DoubleEntendre conversation between V and Frank's father, where she thinks he knows about her job as a prostitute, and is apparently propositioning her to teach his son about sex ("Think you can fit him in?"), before she finally (or rather, misleadingly) convinces him that she's Frank's math tutor.
** Frank's PrecociousCrush on V manifests itself in him being able to walk in on her while she's having a bath, to which neither she nor Frank react with much surprise (the two other boys, who barge in on this scene, are far more shocked).
** V dancing over Frank during the Sock Hop, while wearing a short skirt. Even more absurdly, none of the teachers nor the students comment on the Frank is distinctly ''[[CovertPervert looking upwards]]'' while this happens.
* TookTheBadFilmSeriously: Creator/MalcolmMcDowell acts pretty seriously in comparison to everyone else.
* UncertainAudience: Critics at the time of the film's release noted that it tried to marry elements of a ComingOfAgeStory, a sex comedy, a romance and a thriller without being particularly adept at any of them, with Creator/RogerEbert even pointing the problem out in [[https://www.rogerebert.com/reviews/milk-money-1994 his 1994 review]], which posits the confused tone as a conversation between two studio executives pitching the film.[[note]]Creator/GeneSiskel would outright accuse the film of being made by executives who had an "affinity for hookers".[[/note]] Released in a time (1994) when ComingOfAgeStory works like ''Film/TheSandlot'', ''Film/ThePagemaster'' and the remake of ''Film/TheLittleRascals'' all rode to box-office success, it weaves in elements about a HookerWithAHeartOfGold who is running from the mob and takes refuge in a MeetCute scenario with the protagonist and his father. Too dark to be a family-friendly film (one of the scenes has V openly soliciting for clients to make enough money to get a hotel room for the night), and too much {{Glurge}} to qualify as a comedy-thriller fusion (the third act is motivated by the three boys having to [[DamselInDistress rescue V from her mob boss]], who is holding her at gunpoint, by initiating a fire alarm at a school dance).
* ValuesDissonance: Even with the ''razor-thin'' justification that a ComingOfAgeStory about pre-teen boys who hire a HookerWithAHeartOfGold to flash them may have played well in 1994, further decades of awareness of the challenges associated with TheOldestProfession and much harsher laws designed to protect minors from online predators and sex workers, and this doesn't even have the benefit of being wistful.
* WhatDoYouMeanItsNotForKids: Was possibly supposed to be made as a "romantic comedy". That doesn't quite work when your protagonists are actually three 11-year-old boys![[note]]Siskel and Ebert had a ball speculating on what the pitch meeting must have been like. "It's the raunchy sex comedy ''the whole family'' can enjoy!"[[/note]]
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