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As Beautiful Girls opens, three of the four buddies are having serious relationship trouble. Tommy is dating the devoted Sharon (Mira Sorvino) but seeing his now-married high-school girlfriend (Lauren Holly) on the sly. Paul has just broken up with Jan (Martha Plimpton), his girlfriend of seven years, because she’s “pressuring” him for a commitment. Willie is living with his girlfriend Tracy (Annabeth Gish) but can’t seem to shake his ambivalence about the relationship. Meanwhile, Mo exemplifies healthy family life while Willie’s kid brother and widowed father represent the grim reality of a womanless household.

All three men are stuck—but each at a different point on the dysfunctionality continuum. Tommy’s stagnation is the most clichéd: He’s the loser who peaked in high school, and his old girlfriend evokes bygone glory days. (She’s got little else to recommend her, and she uses the worst come-on line ever: “You can slip into something more comfortable—like me.”) Paul lives in a pinup-strewn room and still listens to A Flock of Seagulls and Split Enz. Willie seems to have left high school the furthest behind him, but when the friends are together, it’s business as usual. They drink heavily, use locker-room slang, rate women numerically, and, at one point, engage in that most dreaded of cinematic events, the group sing-along (to—go ahead and flinch—Neil Diamond’s “Sweet Caroline”)

The film is at its most original when it explores the means that Willie and Paul use to keep adult relationships at bay. Willie falls into conversation with Marty (Natalie Portman), the precocious 13-year-old next door, and soon finds himself utterly smitten with her. His crush is not at all sexual—or even romantic in the traditional sense. He’s simply enraptured with the promise that she represents, and it is to Hutton’s credit that he conveys this complex reaction without coming across like a pervert. Paul uses supermodels the same way Willie uses Marty. That is, he finds it comfortable and nonthreatening to desire them because they don’t represent real-world options. Paul expresses this in a torturously overblown monologue in which he terms the magazine images “hope dancing in stiletto heels.”

Much of Beautiful Girls is concerned with the same truisms about men and relationships that have emerged from every guy-pic from Diner to The Brothers McMullen, though its focus on male ideas about female physicality is somewhat unusual. Inattentive viewers may not even notice that the film’s title is an ironic one; the movie is about how the notion of “beautiful girls” messes up men’s lives. (And it’s beautiful girls, not women, for a reason. These men can’t cope with adult women.) The movie hammers gracelessly and relentlessly at its point: Andrea (Uma Thurman), for instance, appears on the scene for the express purpose of illustrating that beautiful girls are just regular folks, once you get to know ’em. The next day, local girl Gina (Rosie O’Donnell, of course) delivers a fiery harangue about male illusions while brandishing a copy of Penthouse. Ultimately, though, the movie lacks the courage of its convictions: If it were realistic, all its male characters would end up alone at film’s end. CP