This impossible place -- most desired object and least elucidated subject -- makes Molly typical of the women in white guy romcoms.
Sheena was a man,
So I threw him out.
I don't fool around with no Oscar Meyer wiener.
You must be sure that the girl is pure for the funky cold medina.
--Tone Loc, "Funky Cold Medina"
The Hawaii wedding that opens You, Me and Dupree is lavish and lovely. Glowing bride Molly (Kate Hudson) happens to be the daughter of a wealthy real estate developer, known here only as Mr. Thompson (Michael Douglas), and he means to mark the occasion of her marriage to his employee Carl (Matt Dillon) with an expensive, ocean-viewing, perfectly appointed affair. As a crowd of extras gathers to observe, they exchange vows and do appear quite blissful -- if you ignore the part where Carl has to absorb some "stupid son-in-law" jokes by Mr. Thompson.
Minutes later, this buddy movie barely disguised as a romantic comedy begins again, with the couple moved into a picket-fenced home and settled into a newlyweds' rhythm, looking forward to their evenings together while putting up with their day jobs (she's an elementary school teacher, to indicate that she's nurturing as well as beautiful). And then, the wrench: Carl's best friend Dupree (Owen Wilson) announces that he's lost his job, apartment, and car in one swoop, so he's sleeping on a cot at the local bar (inexplicably frequented by Harry Dean Stanton). Oh no, no, exclaims big-hearted Carl, Dupree must stay at his house. That is, his and Molly's house.
And so they arrive home together, even as Molly's adorned in a pale yellow nightie to celebrate Carl's recent promotion by her dad. She's a patient and trusting sort (did I mention nurturing?), and so she agrees to the arrangement, believing her husband that it's "just for a couple of days, a week at the most." It's a little weird when Dupree tells them not to worry about him downstairs on the couch, that he won't be listening to their newlywed activities ("You need to explore each other"), but okay, he's "never been domesticated," as Carl puts it, granting him an odd combination of appeals. His married buddies admire his perpetually adolescent freedom (no curfew, no naggy wife), while women want to take care of him (he's scruffy and he writes poetry).
Soon enough, however, it's clear to Molly and Carl that Dupree is in need of some house-training: he sleeps in the nude on their pricey new couch, leaves dirty dishes, orders HBO, and masturbates using Carl's tube socks and "Asian porn collection." Though he says he's hitting the "job trail, hard," mostly he hangs out with the neighborhood kids, skateboarding and playing street-ball (and inadvertently inspiring a stereotypically lunkheaded bully to beat up a stereotypically unathletic "Asian kid").
Still, Molly tries to be nice, seeing that Dupree laments the loss of his original friendship with Carl, and so she fixes him up with the "Mormon librarian" at her school. This leads to one of the movie's multiple climaxes: Dupree has wild sex aided by butter, candles, and Tone Loc’s "Funky Cold Medina," leading to a fire that ruins that pricey couch and burns down the living room. Molly's beside herself, Carl puts his foot down, and Dupree ends up on a bench in the pouring rain, rejected by the librarian and in some vague state of shock, unable to move.
This begins the movie's second movement, wherein Molly feels sorry for Dupree and Carl gets jealous. She invites him back to the house, appreciates his poetry and cooking skills, not to mention his rudimentary knowledge of wines. Frustrated, Carl finds himself unable to have a conversation without sputtering and calls Dupree a "homo," thus raising the question: why is sensitive, faultless Molly married to him at all? It turns out that he's having trouble at work, too. Because the movie needs to idealize Molly (else why would Carl give up Dupree for her?), it sets up Mr. Thompson as a cartoonish monster, relentlessly belittling his son-in-law. When he suggests Carl get a vasectomy (handing him a brochure with penis-snipping diagrams just a few scenes after he's extolled the value of familial legacies), the film steps off into a deep end of unfathomable illogic.
Or so it seems. The truth is, You, Me and Dupree does follow a set of rules, more or less laid out by movies like Wedding Crashers, The 40-Year-Old Virgin, Failure to Launch, and anything with Ben Stiller, Adam Sandler or Will Ferrell. According to this much-milked formula, the emotionally arrested white manchild provides an endless source of comedy, from farts to pratfalls to prodigious sexual appetites/abilities. Women serve as prizes, long-suffering and gorgeous, because the many hours they spend looking after their infantile lovers don't mean they can't be perfectly toned and coiffed.
In Carl's mind -- because she has no life of her own -- Molly is the precious object in a three-way competition involving her father (who wears silk ties), her houseguest (who's started racing a 10-speed to show his manhood), and her increasingly hapless husband (who does nothing but fret). The movie literalizes Carl's paranoid fantasy when he imagines Molly as a bikinied, high-heeled video ho, with her tongue down Dupree's throat on the deck of her father's boat, named the "Molly and Me" (as he's definitively short on imagination, it could only be that Carl has gleaned such a vision from that porn collection).
This impossible place -- most desired object and least elucidated subject -- makes Molly typical of the women in white guy romcoms. She performs a generic "shock" (mouth agape) at the dinner party where her three men collide, watching her father cuddle up to Dupree (who shares his love for fishing and Lance Armstrong, who long ago proclaimed, "It's not about the bike," even though, in this movie, it is) and her husband go ballistic (he leaps across the table to throttle Dupree). In another movie, you might wonder what's going through her head, but here, you know it's nothing, because it doesn't matter. What does matter is that Carl makes up with Dupree and then makes peace with Mr. Thompson. Only then can he (re)claim his prize, standing on his front porch before a cheering throng of neighborhood children and Dupree, with his bike.
You, Me and Dupree - Theatrical Trailer