To what extent do couples keep secrets from each other? And, if a person finds out something potentially damning about his or her best friend's significant other, should they tell them or simply mind their own business? These are the questions posed by "The Dilemma," a film with more on its mind than the typical romantic comedy, but also one that feels shoehorned in its attempt to generate laughs out of decidedly dark subject matter that doesn't inherently lend itself to a would-be raucous good time. Director Ron Howard (2009's "Angels & Demons") is no slouch as a filmmaker, but he and screenwriter Allan Loeb (2010's "The Switch") come off as desperate on this occasion. They have some fairly incisive things to say about relationships, marriage and friendship, but with every nicely handled, usually dramatic moment, there is one just around the corner that is too broad, over-the-top and juvenile. The schtick, rarely ever funny, does not fit, undermining the material in a way that grows rapidly exasperating.

Owners of upstart business V&B Engine Design, best friends and partners Ronny Valentine (Vince Vaughn) and Nick Brannen (Kevin James) are on the verge of making a big deal with a major automotive company. Even with stress levels high, Ronny has decided it's time to start thinking about proposing to longtime girlfriend Beth (Jennifer Connelly). It is while he is on an excursion to find the right setting to pop the question that he discovers something he really wishes he hadn't: Nick's wife, Geneva (Winona Ryder), carrying on an affair with tattooed, muscled younger guy Zip (Channing Tatum). Ronny confronts Geneva, who admits the truth but also makes it clear that she's not the only guilty party in her troubled marriage. With Geneva threatening to blackmail him if he tells Nick—it turns out they have their own past together no one knows about—Ronny is temporarily silenced, but can't help but dig deeper into his friends' personal lives at the expense of putting his relationships with both Nick and Beth in jeopardy.

There are some succinct ideas at the core of "The Dilemma," but the way in which the picture as a whole is handled is a miscalculation. Ronny is set up as the protagonist, the guy whom the viewer follows and is supposed to be behind, but he is just about the least likable character in the ensemble. The quandary he faces—whether or not to tell Nick about wife Geneva's extramarital activities, and if so, when and how to go about doing it—is a legitimate one, but the choices he makes as he digs himself deeper into their lives are immature and creepy. He spies on and stalks both of them, he steals Geneva's phone right out of her hand to check her text messages, he trespasses at Zip's apartment, he gets into any number of fights involving fists, bats and blowtorches, he selfishly causes a scene during a speech at Beth's parent's fortieth wedding anniversary dinner, and he keeps Beth so in the dark about what he's been doing that she, quite understandably, suspects his prior gambling addiction has returned. As Ronny stands in the middle of the street and wails like an insane idiot in one scene, he loses all credibility as a person worth giving a moment's concern to. Most of this is played for giggles by director Ron Howard, who doesn't understand he should have been making a penetrating "what if" drama all along rather than the forced, disingenuous comedy it actually tries—and fails—to be. Suffice it to say, all the malarkey with Ronny falling into poisonous plants at a greenhouse and suffering the physical consequences would have been wise to leave on the cutting room floor.

At least Ronny eventually does see the error of his ways. As the film leads toward his attempts at redemption, those loved ones around him aren't shy about pointing out the mistakes he's made along the way. It is here, then, that the film, too, redeems itself enough to not be a total wipeout. Save for a terrible scene where Ronny is beat up right before an all-important business presentation, the movie dodges the expected break-up-and-make-up clichés for genuine, level-headed adult conversations, the characters finally given the intelligence to say what real people in similar situations might say. There are other strong moments as well. Ronny's diner chat with Geneva after he's found out about her affair is terrifically written and performed, with the balance of power shifting between them when Geneva proves to be playing with a fuller deck than he'd anticipated. A climactic scene where truths are finally spoken is also delicately, but effectively, handled, cementing that Geneva does deeply care about her husband even as they must acknowledge that sometimes there is no hope in mending a broken marriage.

Vince Vaughn (2009's "Couples Retreat") and Kevin James (2010's "Grown Ups") are just playing close variations of the same archetypical personalities their roles usually call for, and so there isn't enough of a stretch for them to impress as Ronny and Nick. It's just as well anyway, since their female co-stars are the standouts. As culinary chef Beth, Jennifer Connelly (2010's "Creation") hasn't been this loose and free in a film in at least the better part of a decade; she still remains the emotional center, but she also looks to be having fun, getting a chance to smile and laugh and cavort in a way that her usually deadly serious acting work rarely gives her the chance to do. Making a comeback in a big way with her rattling supporting turn in 2010's "Black Swan" and her larger part here after several years of keeping a low professional profile, Winona Ryder (2009's "The Informers") steals scenes left and right. It would have been easy to portray Geneva as a two-dimensional bad guy, but Ryder and the script don't let this happen as the character's yearnings, disappointments, desperation and guilt help to shade her with a soul and welcome sympathy.

Well shot on location in Chicago by Ron Howard's director of photography regular Salvatore Totino (2008's "Frost/Nixon"), "The Dilemma" has exactly two funny moments, both of them featured in the theatrical trailer. One involves Ronny's confusion between Helen Keller and Sybil when he tries to accuse Geneva of having split personalities, and the other concerns the cheerful piping-in of unsuspecting Cousin Betty (Grace Rex) during Ronny's anniversary dinner speech. Comedy-wise, nothing else works, and it frequently becomes mighty uncomfortable as the random, inappropriate hijinks are met with the audience's silence. Had director Ron Howard reevaluated his approach to the story, he might have had something solid on his hands. It's clear when a film is being tonally dishonest with itself, and this is what overpowers the positive traits that "The Dilemma" has to offer.