Boys to men.

Filmmakers of three new films--L.I.E., Eban and Charley, and Our Lady of the Assassins--talk about why they chose to portray teenage boys' relationships with older men. Is it a rite of passage or just plain wrong?

As far as pop culture is concerned, if a straight teenage boy hooks up with an older woman, it's a veritable rite of passage. When Finch (Eddie Kaye Thomas) tumbled with Stifler's mom in the first American Pie, it was an excuse for triumphant giggles; when young Pacey (Joshua Jackson) bedded his high school teacher in the first season of the WB network's Dawson's Creek, it was an occasion for swoony tea and sympathy. But let a gay teen suggestively eye an older man--and let the older guy reciprocate--and the creepy music is cued. The sexual vultures tempted by the young hustlers in movies like My Own Private Idaho and johns are a distasteful lot, and even the apparently affectionate relationship between a 30-something man and a 17-year-old boy in the new thriller The Deep End leads to tragedy.

Advocates for gay youth have their own reservations about intergenerational encounters. "We maintain a strict policy prohibiting any relationships between the youths we serve and the volunteers and staff, partly to protect our organization but also to protect the youth," explains Bryant Hilton, a board member of the Out Youth support group in Austin, Tex. "We discourage relations with other adults as well. The kids we serve first need a safe place to figure out who they are, so [relations with older men] isn't something we see as much of an issue."

More teens are now coming out at a younger age, Hilton acknowledges, so they may well first encounter sex among their peer group rather than seeking out an older tutor. Still, if straight boys are allowed to fantasize about older women, why has gay-themed pop culture been slow to grant queer boys their own Summer of '42? Showtime's Queer as Folk finally crossed into that territory last December when, following its British template, it depicted underage Justin (Randy Hanison) avidly pursuing 29-year-old Brian (Gale Harold); as Justin was fond of pointing out, he was in ways more mature than the perennially adolescent Brian.

Three movies are now following QAFs lead. The young men who encounter older men in L.I.E., Our Lady of the Assassins, and Eban and Charley range from desperate street kids to suburban youths, but they speak to a universal experience: They are all sexually curious; they seek escape from oppressive surroundings; they yearn for emotional connections.

The older men they encounter are more various. In the laid-back romance Eban and Charley, due out November 9, Eban (Brent Fellows) is at age 29 a bit of a lost soul himself--a sacked teacher with an inability to relate to anyone but younger boys. In contrast, Our Lady of the Assassins (which opens September 7) has as its protagonist the worldly-wise Fernando (German Jaramillo), an erudite, melancholic writer in his 50s; he returns to his hometown--the violent, crime-ridden Medellin, Colombia--expecting to die, only to rediscover his passion for life when he invites a young hustler (Anderson Ballesteros) into his bed and his life.

Big John Harrigan, played by the formidable Brian Cox in the Long Island--set drama L.I.E. (opening September 7 in New York City), is the most problematic of the lot: A bluff former marine who banters easily with the Irish-American cops in his community, he's also an admitted pedophile who uses his red Cutlass 442 to bewitch the local boys. But even in Big John's case, it's not always clear from moment to moment who exercises the control in his relationships: Fifteen-year-old Howie (Paul Franklin Dano) tests his own seductive wiles by reciting a Walt Whitman poem to his older admirer.

"When he reads that poem, I always felt he's very aware of what he's doing, the power he has over Big John," says L.I.E.'s first-time director and cowriter, Michael Cuesta. "When Howie starts testing his own sexual prowess, it was really inspired by the way [Vladimir Nabokov's] Lolita uses her sexuality over Humbert Humbert. Part of Howie's awakening is his becoming aware of his prowess over this older guy--who's a predatory, strong figure. Howie discovers an ability to manipulate John."

While there is no future to their relationship--Big John dismisses a slightly older boy whose bloom of youth has begun to fade--Cuesta presents his cautionary tale as a coming-of-age for Howie, whose ultimate sexual orientation is left ambiguous. "There are guys out there like Big John who are predatory but who are also pillars of the community," says Cuesta. "The fact that he is so human and accessible makes him that much scarier. But John is an antihero too. In a way, he helps the boy when he sends him off like a marine to confront his dad."

A dramatic age disparity between an older man and an adolescent shouldn't automatically be dismissed as pedophilia, says Our Lady director Barbet Schroeder (best known in this country for 1990's Reversal of Fortune): "Pedophilia," he insists, "has nothing to do with this story."

Upon meeting street-savvy, hair-trigger teenager Alexis (Anderson Ballesteros), the older Fernando first strikes a financial bargain--offering meals, a place to live, CDs but it leads to a deeper attachment. "An adolescent [like Alexis] is completely aware of the world and of himself," says Schroeder. "It's really an impossible love story--they come from very different backgrounds, but they learn from each other. Fernando learns about the new realities of his town--the paradise of his childhood that has been transformed into some kind of hell. And the boy has an admiration for this adult who is an iconoclast and a rebel. It's a learning situation for both of them. It's deeply homosexual to the core--after all, [such relationships were] one of the bases of Greek culture."

While Our Lady takes place in a shadowy, almost operatic world, the Pacific Northwest setting of Eban and Charley is deceptively casual and drably common-place, making its love story, between the 14-year-old Charley (Giovanni Andrade) and the older Eban, all the more subversive. Inspired by a real-life incident--first-time director James Bolton cites a young friend of his who was dumped by an older boyfriend because the older guy's pals disapproved of their age disparity--the film is moonily romantic, with Charley ardently pressing the affair even when Eban tries to cut it off.

Argues Bolton, "Some boys mature faster than others--they know they're gay, they want to have relationships, and they do. Charley is definitely aware, and he pursues Eban. This whole age-of-consent thing is really all about a number. It's possible for these kinds of relationships to work. Sure, a lot of them don't, but that doesn't mean they can't." Bolton admits such partnerings are often "demonized, but that's all because of fear, motivated by misunderstanding. It's important to work these issues out."

The notion of underage teens having gay sex--whether with their peers or with someone older--may be disquieting to many, but sex itself isn't really the point of this trio of films, all of which are relatively chaste. Our Lady is the only one to actually follow its lovers into the bedroom, for some discreet lovemaking. In L.I.E., Big John, though a threatening presence, never quite makes a move on Howie. And in Eban and Charley, Bolton purposely cuts away from actual sex so as not to lose the film's focus on the couple's underlying emotional drama.

The filmmakers all seem to borrow from E.M. Forster's famous dictum: "Only connect." In Eban and Charley, that connection is so immediate it echoes many a past romantic melodrama: Two lovers buck the odds and ignore social proscriptions. In Our Lady, connection gives way to metaphor: The young hustler actually serves as a tour guide through the living hell of Medellin. "Instead of discovering death," explains Schroeder, "Fernando discovers something worse--a horrible pain. And through his pain we discover the pain of the whole country."

And in L.I.E.--potentially the most controversial of the three, a possibility Cuesta will face head-on when the film opens at strip-mall multiplexes along its titular Long Island Expressway--a pedophile is nearly redeemed as he redirects his seduction scenario to become a positive father figure for Howie. "It really is a film about the need to connect," says Cuesta about his film's daring gambit. "Love comes in many faces."

Kilday is film editor for The Hollywood Reporter.