Many comedies play with the premise of ethical correctness and honesty in a personal relationship, and most of them do it better than Ron Howard in The Dilemma. Known primarily for darkly emotional, psychologically loaded, and frequently Oscar-nominated films like Apollo 13, A Beautiful Mind, and Cinderella Man, Howard hardly seems like the ideal choice to direct a slapstick family comedy starring Vince Vaughn. This might lead you to expect some kind of interesting twist or profound new level of interpretation, but unfortunately that is not the case.
The plot has a certain degree of potential for engaging hilarity, if only the script were sharper, wittier, and simply better thought through. Ronny (Vince Vaughn) and Nick (Kevin James), old college friends who now run and auto business together, are both in happy relationships. Ronny is dating the impossibly sexy Beth (Jennifer Connelly), and Nick is married to the lovely Geneva (Winona Ryder). It seems apparent from the start that both men are with women who are way out of their league, and it is one of the conceits of this film that this issue is never really touched on. Frankly, the guys are losers; both far from being tanned body-builders, with only a vague semblance of a career. The women on the other hand, are shown as driven, put-together, impeccably dressed and made-up, looking more like actresses than homely housewives. Already the film has the makings of a fantasy.
The more ambitious of the two friends, Ronny strives to further their business prospects and manages to wrangle a meeting with an important automobile company to show off their ideas. The timid and self-deprecating Nick is nervous and intimidated and quickly goes off into a spiral of panic attacks and bouts of spontaneous cursing. Ronny, meanwhile, still deciding whether he has the drive to marry the gorgeous Beth (seriously?), accidentally comes upon Geneva making out with another man (Channing Tatum). Somehow, we are supposed to be shocked that the attractive, vibrant Geneva is cheating on her overweight, debilitatingly neurotic husband with an uncomplicated younger man. In any case, Ronny is horrified, and has trouble deciding whether it is his ethic responsibility to tell Nick the truth, especially as he is preparing for a presentation that can be vital to both of their careers.
It is hard to tell whether Ronny’s reticence is driven more by friendly solicitude or a callous fear that Nick will have a meltdown and botch the meeting. As Ronny gets himself deeper and deeper into Nick and Geneva’s affairs, resorting to spying, stalking, and other unsavory techniques, the narrative grows rather cringe-worthy than hilarious. It is apparent that both Nick and Geneva are at fault here, but Geneva is supposedly more devious because she has a hot young lover, oddly named Zip, who bursts out crying when Ronny “hurts his feelings”. Perhaps we are meant to realize that any woman with the gall to date someone named Zip is undeserving of a kind, sensitive man like Nick.
The whole situation culminates in a confrontation/screaming match between all concerned, and by that time you may want to join into the verbal and physical abuse on screen. The relationships between the characters are never defined clearly enough and we are force-fed much more than we are actually shown. The characters remain decidedly one-dimensional and not really very funny. In the end, we are meant to accept the justice and inevitability of all that ensues and perhaps go away pleased that we do not have a friend like Ronny.