To tell or not to tell is the question for about five minutes of The Dilemma, and the rest of the time is spent with a character waiting for the opportune time to tell his best friend that the guy’s wife has been cheating (that he finds the least opportune and appropriate time to do is not mandatory for comedy or drama but certainly a cheap way to try to force both). That situation in a feature-length comedy, of course, means that there must be transparently contrived obstacles on top of transparently contrived obstacles.

The conflict in the delay, though, comes not from those obstacles, which Allan Loeb’s screenplay half-heartedly attempts to incorporate as part of the character or his relationships with others, but from the protagonist’s bumbling efforts to keep himself clean (he worries his friend might “kill the messenger,” especially a messenger who once slept with the message-receiver’s wife and never got around to telling him), nab proof of the wife’s infidelity, and, oh, let’s throw in a bunch of lies that lead the guy’s girlfriend to suspect that he’s had a relapse of his gambling addiction. Yes, that will do.

Beyond those elements, there’s something inherently discomforting about Ronny Valentine (Vince Vaughn), and if you think that name suggests he’s a salesman of sorts, you’re correct in the assumption. He sells the concept of prototype engines to major auto manufacturers, while his best friend in the whole, wide world, Nick Brannen (Kevin James), does all the work of designing and building them.

They’ve just struck a major deal to create an all-electric engine that has the same sound and vibration quality of the ones found in classic muscle cars. There’s pressure all around: If they succeed, they’ll receive an exclusive contract; Ronny is thinking about getting ready to get over his commitment issues and ask his girlfriend, Beth (Jennifer Connelly, who, you know, is exactly the type of woman to inspire such uncertainty, the man said with disbelief); and to top it all off, Ronny spots Nick’s wife Geneva (Winona Ryder) making out with another man (Channing Tatum, playing the sensitive-but-still-a-cad cad Zip).

His unfortunate discovery occurs in a botanical garden, where, startled by the unfolding events, he falls into a grouping of poisonous plants, which results in a blotchy, bumpy rash, painful urination, and, well, you get the picture. Thus begins Ronny’s web of lies and deceit, telling Beth that some plants scraped him while he was attempting to retrieve a ball for some overweight kids (cuts away to his story are probably parts of a different draft of the script that actually puts some perspective into Ronny’s addiction and come across awkwardly here). He later says he only started lying to her because he learned she didn’t mention to him that a career opportunity opened up for her in Vegas, although since that revelation comes later, that’s another lie — one the movie generously ignores.

Ronny isn’t a terrible person, because he’s torn. He’s kind of torn, maybe? Either way, he’s definitely not as bad as Geneva, who threatens to lie to Nick that Ronny has been hitting on her for decades if Ronny tells his best, most beloved friend in the whole, wide world that she’s been unfaithful. Then she shows him how she’ll cry crocodile tears, and she goes from a wounded woman, who confesses (honestly) that Nick has been receiving some extra attention and gratification at a local massage parlor, into full-blown, off-putting villain mode.

Then again, Geneva doesn’t begin stalking anyone the way Ronny stalks her and Zip, sneaking onto the guy’s balcony and snapping pictures of the two in the middle of their betrayal. Ronny also decides to use a party for Beth’s parents’ fortieth wedding anniversary to rail on and on about honesty in an accusatory and occasionally assaultive tone. From those actions of what really amounts to a drawn-out breakdown arises the wild stabs at comedy.

In focusing the machinations of blatant plot-building on this unstable character, The Dilemma borders between a movie that is simply without naturally occurring humor and one that starts to get a bit creepy.

Mark Dujsik is a member of the Chicago Film Critics Association and the Online Film Critics Society. For more of his reviews, visit his website.

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