There are many puzzles to be solved in the contemporary social comedy The Dilemma. The most pressing is how director Ron Howard, who has tackled difficult historical and biographical material with slick, Oscar-winning professionalism, could miss such an easy lay-up. You can't fault the production. This is high-gloss stuff, very well shot with a fairly grown-up performance by Vince Vaughn as an automotive entrepreneur burdened with the knowledge that his best friend's wife is cheating on him. The central question for the characters is one of honesty. Guy has best friend. Guy sees best friend’s wife making out with young hunk. Should guy tell best friend? Sorry, but despite what you may have seen in the lame trailer, that’s not the real dilemma in The Dilemma. Nope, the far more puzzling question is: Since this emaciated premise is the entirety of the script, where the hell is the movie?
At 6'5", Vince Vaughn isn't just a tall drink of funny. He's a hurricane of flip asides and sincere sarcasm. He'll double talk his way out of anything and his ability to surprise us with a line reading can reach Walken-esque heights. The force of Vaughn's aggressive presence can subsume a movie, which is usually welcome because he can be so damn entertaining. In The Dilemma, the mile-a-minute humor remains, yet his commitment to his character, Ronny Valentine, outpaces any desire to be snarky for snarkiness sake. Ronny runs the B&V Engine Design company with partner and college best friend, Nick (Kevin James). The pair is on the verge of landing a deal with Chrysler that would put their business on the map and allow for eternal bachelor Ronny to propose to girlfriend Beth (Jennifer Connelly). Even with the help of Susan, a phallic-obsessed car consultant (Queen Latifah), Ronny and Nick are under enormous pressure to deliver their product on time. While scouting an arboretum as a place to pop the question, Ronny spies Nick's wife Geneva (Winona Ryder) making out with another man. To devastate the overworked Nick with news of Geneva's paramour would make it impossible to close their big money deal. Not telling Nick means keeping a major secret from his best friend; hence the movie's title.
Over to Vince who, unwilling to break Kevin’s heart directly, decides to confront Winona. Still looking bad but sounding quite reasonable, Winona tells him: “You do not know what goes on behind the curtain of a marriage.” What’s more, she adds that Kevin is a regular frequenter of tawdry massage parlours, a revelation that appears to upset Vince a whole lot more than her. Hey, bromances being what they are, Vince’s sharp pang of disappointment might have been worth pursuing but, Ron Howard being who he is, not a chance.
Instead, the plunge continues, from one clumsily executed set-piece to another – here a big brawl, there an anniversary party, on to a PowerPoint presentation, then a group intervention. At all of these stops, spurred on by mounting evidence that the flick bypassed the script stage, Vince is encouraged to improvise, which, erring on the side of generosity, he does to self-indulgent excess.
The Oscar-winner (A Beautiful Mind) pulls the movie down to earth in every scene she's in. Her disappointment and confusion after Ronny ruins her parent's anniversary party with his passive-aggressive (and funny) toast, reminds us we haven't completely lost interest in the stakes. These stakes are established in the very first scene with the question, "how well do you really know someone?" The crucial query for The Dilemma is how well does it know itself? Here's a film that toys with its darker side, but lacks the nerve to go where the material is taking it.