What do you get when your meet cute involves horny tweens and questionable boundaries? This thing.

How Did This Get Made? has celebrated almost nine glorious years of comedians parsing movies that shouldn’t exist, but somehow do, largely through sheer force of will. Sometimes the titles discussed turn out to be underrated gems, but most remain a shocking waste of money, time, and film stock. Yet somehow, even after more than two hundred full-length episodes, they still haven’t covered one of the most baffling mainstream comedies of the nineties, 1994’s Milk Money.

It’s okay if you don’t remember Milk Money. Sometimes I wonder if I hallucinated it during the time when I caught adult chicken pox, until I remember Roger Ebert’s hilarious review of it. I’ve only seen it once, but will never forget the goosebump-raising discomfort it caused me. Now, there’s nothing wrong with uncomfortable movies. Movies like Hereditary and Antichrist, those are supposed to make the viewer uncomfortable. A lighthearted romantic comedy about a kid who wants to find a wife for his widowed father should not make anyone feel uncomfortable. Nevertheless, watching it makes one grimace in the same way as drinking orange juice immediately after taking cold medicine.

When you consider the plot of Milk Money, you might find yourself asking, indeed, “How did this get made?” My guess is that screenwriter John Mattson (who would go on to write two sequels to Free Willy) wanted to do his own versions of Pretty Woman and Sleepless in Seattle, wrote down about half a page worth of notes for each one, then decided “fuck it, I’ll just combine them.” For this, he was paid $1.1 million dollars, a record for a romantic comedy at the time. You might ask “Who is this for?” to which I can only answer with a perplexed shrug. It’s purportedly a romantic comedy, but isn’t romantic or funny. It tries to be both heartwarming and cheeky, and succeeds at neither. It’s not a kids’ movie, but a lot of time is spent focused on its tween co-star, the catalyst that brings the two romantic leads together.

That would be Michael Patrick Carter as Frank, and Frank and his buddies, they gotta, have to, need to see some naked tits. Living in an “only in the movies” picturesque small town where neither cable television or Playboy exists, their only recourse is to pool together their titular milk money and travel into the big city to pay a woman to show them her goods. This is treated as a familiar rite of passage — sure, don’t you remember when you were 12 and you hired your first hooker? It’s just like when you make your Confirmation, or your dad shows you how to shave, even though you don’t have any facial hair yet.

Frank and the other boys have surprisingly little trouble finding someone to agree to their scheme. That would be V (Melanie Griffith), the kind of Hollywood prostitute who only has one client that she pointedly does not have sex with. Though she’s committing a felony, V finds the boys utterly charming, and indulges them in their request. An embarrassed Frank covers his eyes at the last minute, which is good, because otherwise what happens next would be really gross and weird, instead of merely kind of gross and weird.

That this light “a big city gal is gonna shake up this small town” comedy could easily turn into some sort of Dogtooth-esque nightmare about twisted family relationships is just one of many issues with Milk Money.

Based largely on the fact that she gives the boys a ride home, Frank has decided that V would make the perfect wife for his father, Tom (Ed Harris), and a mother for himself. Whether it’s a failure in screenwriting or direction, Frank’s feelings for V come off as a little vague. He immediately sets her up as his surrogate mother (because apparently he’s utterly bereft of aunts, grandmothers, teachers, or even just a friend’s parent), but also looks at her with dewy-eyed adoration, like he’s thinking maybe he’ll marry her someday, if she’s willing to wait six or seven years. That this light “a big city gal is gonna shake up this small town” comedy could easily turn into some sort of Dogtooth-esque nightmare about twisted family relationships is just one of many issues with Milk Money.

Through a series of contrivances so dumb they’re not worth explaining, Frank moves V into his treehouse, telling Tom that she’s his math tutor, which Tom buys without question. Milk Money is the kind of comedy that only works if you’re willing to accept that every character is a complete idiot. Just a mismatched shoes, unable to use a fork without stabbing themselves in the face nincompoop. The plot can’t move from point A to point B without the characters constantly talking around each other and never on the same page as to what they’re talking about.

That’s a labored gag at the best of times, but here results in a real Maalox Moment of a scene in which Tom and V are talking about her job, which Tom believes is a math tutor, and V knows is prostitution, but Frank has neglected to tell her that he lied to Tom about what she does for a living. “I would teach him myself, but I’m way out of practice,” Tom says, as a piece of the viewer’s soul breaks off screaming, and V just accepts it without question.

V pretty much accepts everything that happens to her once when she arrives in Frank’s town. A kid she’s just met who paid to look at her tits latching himself onto her and all but demanding that she adopt him? That’s fine. That same kid asking her to put on a dress that once belonged to his dead mother? Absolutely. Being nudged towards that kid’s dad in a scheme to get them to fall in love and marry? No problemo! Everything, even donning a nude body stocking and letting Frank take her to school to use as a human mannequin in a science class presentation, is all part of the plan to get V to realize that this is the life she really wants, a life of suburban respectability with a ready-made family and a closet full of granny dresses, where everyone tells her that she looks like Grace Kelly (which she does not, not one little bit).

Milk Money is one of those movies that ham-handedly suggests that, really, all women have a maternal streak in them, it just takes the right chipmunk-cheeked kid to bring it out. It doesn’t matter that V’s interactions with Frank have an unpleasant sexual undertone to them, such as when she tells him “There’s a place where you can touch on a woman that will drive her crazy. Her heart.” The audience is supposed to be moved by V and Tom coming from two different worlds to fall in love and make a family for Frank, a family that, the way things are going, will end up destroyed after a father-son knife fight for V’s affection at Thanksgiving.

There’s also some nonsense about V being chased down by a mob boss played by Malcolm McDowell, but it doesn’t matter, it’s just one more thing the movie tries and fails. It also results in V finding a literal bag of money that allows her to simply buy the respectability she craves and stay with Tom and Frank forever. There’s not a single plot twist, turn, or beat in Milk Money that isn’t calculating and smarmy. It’s a movie in which one of the main characters is a prostitute, yet is coy about what exactly a prostitute is. For the overall impact it has on the plot and its outcome, V might as well be a musician, or a Mary Kay saleswoman.

It doesn’t matter. It exists largely so the film could be sold as a spicy romantic comedy that you could still show to your grandmother, if your grandmother had no taste. It’s not spicy, however, it’s sleazy, with a bland, boring center, and Paramount paid $1.1 million for it.

Milk Money Trailer: