Most Similar Movies to The Dilemma (2011)
If you are looking for movies like The Dilemma (2011), you might like movies tagged with keyword : comedy, drama, friendship, betrayal, marriage, deception, moral dilemma, chicago, bromance, midlife crisis, secrets, trust, relationships, choices, american film, adult comedy, emotional conflict, life crisis, humor, tension .
The Best Man (1998), The Climb (2019), Afternoon Delight (2013), Babysplitters (2019), The Romantics (2010), The Upside of Anger (2005), Hindsight (2015) ... Let's take a look at the following list...

The Best Man (1998)
A pretty Italian (Ines Sastre) weds a wealthy businessman (Dario Cantarelli) while pledging herself to his best man (Diego Abatantuono).
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The Climb (2019)
Two lifelong pals test the boundaries of their friendship when a woman comes between them.
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Afternoon Delight (2013)
Rachel tries to spice up her marriage with a trip to a strip club. She befriends McKenna who gave her a lapdance. She moves in with Rachel's family and becomes a nanny for the son.
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Babysplitters (2019)
When two couples with mixed feelings about having kids hatch a plan to share one baby, it seems like the perfect compromise-until things spiral out of control.
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The Romantics (2010)
Seven close friends reunite for the wedding of two of their friends. Problems arise because the bride and the maid of honor have had a long rivalry over the groom.
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The Upside of Anger (2005)
When her husband unexpectedly disappears, a sharp-witted suburban wife and her daughters juggle their mom's romantic dilemmas and family dynamics.
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Hindsight (2015)
After a strange elevator ride, a woman gets a chance to re-live part of her life.
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How to Save a Marriage and Ruin Your Life (1968)
When a carefree bachelor tries to get his best friend to drop his mistress and return to his wife, he finds himself with romantic problems as well.
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One Wild Moment (2015)
Two friends bring their daughters with them on a beach vacation and find themselves in an awkward situation. A remake of the 1977 film "Un moment d'égarement".
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Stolen Heart (1998)
A trio of small-time hoods decide to go for the big time by kidnapping the daughter of a rich self-help guru. The kidnapping goes awry and the whole group find themselves in the midst of a family relationship problem.
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The Groomsmen (2006)
A groom (Ed Burns) and his four attendants wrestle with issues related to friendship and maturity a week before the big day.
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Humpday (2009)
Two guys take their bromance to another level when they participate in an art film project.
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The Oranges (2011)
The enduring friendship between the Walling and Ostroff families is tested when Nina, the prodigal Ostroff daughter, returns home for the holidays after a five-year absence and enters into an affair with David, head of the Walling family.
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Easy (2016)
An anthology series set in Chicago explores the landscape of modern relationships.
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Home Sweet Hell (2015)
Don Champagne seems to have it all, but when his wife, Mona, learns of his affair with a pretty new salesgirl, she will stop at nothing to maintain their storybook life.
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Serious Moonlight (2009)
A high-powered attorney duct tapes her adulterous husband to the toilet ... right before their home is invaded by burglars.
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Such Good People (2014)
A young gay couple discovers a secret room filled with cash while house-sitting for a rich couple who die while out of the country.
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Sideways (2004)
Two men reaching middle age with not much to show but disappointment embark on a week-long road trip through California's wine country, just as one is about to take a trip down the aisle.
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