Let's dispense with the central question posed by Friends with Benefits right away. In the world of the contemporary Hollywood romantic comedy, it is in fact not possible for two straight BFFs of the opposite sex to sleep together and not fall in love. In charting the relationship of New York headhunter Jamie (Mila Kunis) and her latest professional catch, L.A.-transplant art director Dylan (Justin Timberlake), from pals to no-strings-attached fuck buddies, from estranged ex-friends to partakers of true love, Will Gluck's film spares no platitude. Any interest (and it is minimal) in following the familiar trajectory derives from the movie's meta-critique of the rom-com, a foregrounding of the generic clichés that it will then itself shamelessly deploy.
Early on in the film, Jamie and Dylan bond over their weariness with dating (they've both recently been dumped) and the lying nature of Hollywood romances (they're watching a parody of a romantic comedy that deliberately renders absurd the genre's signature strategies.) While Dylan mocks the musical cues that tell the audience how to feel, Jamie wonders why they don't make movies "about what happens after the big kiss." Dylan's response is typically obfuscating—and unfunny: "They do. It's called porn." Actually, there's a rich cinematic tradition of films about what happens to relationships once the initial romance wears off (King Vidor's The Crowd standing as arguably the crowning example), but given that Gluck's movie's cinematic touchstones are Pretty Woman and It Happened One Night, we can be pretty sure that this project won't take us any ways beyond the inevitable "big kiss."
The Garry Marshall and Frank Capra films figure as personal favorites of Jamie's who, despite her bitterness with love, is still firmly committed to the idea of a Hollywood-style romance. Nor does she make any bones about living her life according to lessons learned from such movies. She tells a potential boyfriend that she won't sleep with him until the fifth date, a strategy she says she picked up from a film. It's made fairly clear that what's holding Jamie back from romantic success is her need for life to conform to cinema, a dream scenario hatched as a reaction to her promiscuous mother's casual approach to sex. (The older woman is glimpsed watching what we can assume is her own cinematic touchstone, Paul Mazursky's 1969 spouse-swapping comedy Bob and Carol and Ted and Alice.)
Dylan's own issues have to do with a fear of commitment (and, in a dismal side plot, a father suffering from Alzheimer's), thus ensuring that both lead characters' obstacles to romance adhere strictly to tired gender stereotypes. The male lead's sexual identity is further complicated by his fears of being thought gay (homophobic panic being no stranger to contemporary mainstream comedy). Self-conscious about his sexual practices (apparently he likes a finger up the ass), his former enthusiasms (Harry Potter), and even his need to take an assertive role in the sack (he tells Jamie he feels "emasculated" when she mounts him), he's frequently mistaken for queer as well, most memorably by gay coworker Woody Harrelson, who, upon first meeting him, suggests the two go "trolling for cock." Harrelson provides some of the film's few genuine laughs, but even as he destabilizes the notion of heterosexual romantic love by positing gay life as an alternative norm, he ultimately confirms the safer conception, delivering platitudinous speeches to Dylan about the importance of traditional coupling.
In the end, Dylan's homophobic hang-ups are dismissed as summarily as the film's genre critique. Dylan and Jamie eventually go from fucking to "making love," the difference made clear in Gluck's decision to shoot the latter sequence in an oozy, dissolve-happy succession of close views of coupled flesh set to a dismal folk-rock song on the soundtrack. As the film's meta concerns recede, the platitudes pile up, culminating in successive sequences of parental advice—motherly for Jamie and fatherly for Dylan—containing such jewels as "Life's too short and you can't waste a minute of it." So much for tweaking cliché.
In encouraging her to settle in with Dylan, Jamie's mother may chide her for wanting a fairy-tale romance, but rather than take this as a critique of living one's life via rom-com formula, Gluck allows Jamie the very possibility that he pretends to dismiss. As Dylan stages an all-out spectacle to win his temporarily estranged buddy back to his heart, he tells her "I know you wanted your life to be like a movie," an aspiration which the film seems to then endorse as a perfectly reasonable set of demands. With the ending of Gluck's film mirroring the conclusion of the parody rom-com the two had been watching (with the crucial difference that the "real" event takes place at the authentic Grand Central Station and not the soundstage stand-in of the film-within-the-film), life indeed proves to be just like the movies, even if the newly formed couple can't manage to snag the hansom cab secured by their on-screen counterparts. For a film that had once made some pretense toward exposing such dangerously submissive attitudes toward Hollywood romance, Friends with Benefits's conclusion can't help but seem more than a wee bit disingenuous.