Best movies like The Dilemma

Two best friends. Nothing could come between them... or could it?

A unique, carefully handpicked, selection of the best movies like The Dilemma Starring Vince Vaughn, Kevin James, Winona Ryder, Jennifer Connelly, and more. If you liked The Dilemma then you may also like: You Will Meet a Tall Dark Stranger, Waking Up in Reno, We Don't Live Here Anymore, Wedding Crashers, Wedding Daze and many more popular movies featured on this list. You can further filter the list even more or get a random selection from the list of similar movies, to make your selection even easier.

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Longtime friends Ronny and Nick are partners in an auto-design firm. They are hard at work on a presentation for a dream project that would really launch their company. Then Ronny spots Nick's wife out with another man, and in the process of investigating the possible affair, he learns that Nick has a few secrets of his own. As the presentation nears, Ronny agonizes over what might happen if the truth gets out.

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You Will Meet a Tall Dark Stranger

Two married couples find only trouble and heartache as their complicated lives unfold. After 40 years of marriage, Alfie leaves his wife to pursue what he thinks is happiness with a call girl. His wife, Helena, reeling from abandonment, decides to follow the advice of a psychic. Sally, the daughter of Alfie and Helena, is unhappy in her marriage and develops a crush on her boss, while her husband, Roy, falls for a woman engaged to be married.

Waking Up in Reno

Candy and Lonnie Earl are just crazy about each other. The problem: she's married to Roy and he's married to Darlene. So far it's been a secret affair. But that's about to change, because this foursome is driving cross-country and headed for some big surprises.

We Don't Live Here Anymore

Married couple Jack and Terry Linden are experiencing a difficult period in their relationship. When Jack decides to step outside the marriage, he becomes involved with Edith, who happens to be the wife of his best friend and colleague, Hank Evans. Learning of their partners' infidelity, Terry and Hank engage in their own extramarital affair together. Now, both marriages and friendships are on the brink of collapse.

Wedding Crashers

John and his buddy, Jeremy are emotional criminals who know how to use a woman's hopes and dreams for their own carnal gain. Their modus operandi: crashing weddings. Normally, they meet guests who want to toast the romantic day with a random hook-up. But when John meets Claire, he discovers what true love – and heartache – feels like.

Wedding Daze

After losing the woman of his dreams, Anderson is convinced he'll never fall in love again. But at the urging of his best friend, he spontaneously proposes to a dissatisfied waitress named Katie and an innocent dare evolves into the kind of love that both have been looking for all along.

The Oh in Ohio

Priscilla and Jack appear to be the perfect couple, but they have a secret: She is sexually frustrated. They separate in the hope of resolving the situation. While Jack moves into a bachelor pad and begins an affair with a student, Priscilla discovers the joys of self-pleasuring and finds an unusual bed-mate.

The Other Woman

After discovering her boyfriend is married, Carly soon meets the wife he's been cheating on. And when yet another affair is discovered, all three women team up to plot mutual revenge on the three-timing SOB.

Just Looking

It's 1955. Lenny is a 14-year old boy who is totally fascinated by sex. He is too scared to "do it," so he dedicates his summer to seeing two other people do it. Easier said than done. Caught in the act of spying, his mother and stepfather ship him off to spend the summer with his aunt and uncle in "the country" -- Queens. His plan looks like a bust and his summer seems destined for boredom, until he meets a whole new group of friends -- young teens who have a "sex club."

Best Friends

Two young couples taste the "free and easy" life on a cross country motor-home tour until love backfires and tragedy follows.

Meet Bill

A mild-mannered bank executive mentors a teenage con artist and tries to make a career change as a doughnut merchant.

Blame It on Rio

Matthew Hollis is man on holiday in Rio with his best friend. Both men have teenage daughters with them. When Matthew falls for his best friend's amorous daughter named Jennifer, they embark on a secret, if slightly one-sided relationship. Jennifer's father is furious when he finds out about the 'older man' in his daughter's life, and sets out to hunt him down with the aid of Matthew!

The Burning Plain

A trailer is burning in the middle of a plain. The bodies of two adulterous lovers are found. Scenes from both families, before and after the dramatic events, suggest an unusual connection between them. But what is their secret?

Butterfly on a Wheel

A sociopathic kidnapper methodically pushes a desperate pair of parents to their absolute breaking point.

Cool and the Crazy

Unhappily married couple Roslyn and Michael lead separate affairs that lead to violent repercussions for all.

Couples Retreat

Four couples, all friends, descend on a tropical island resort. Though one husband and wife are there to work on their marriage, the others just want to enjoy some fun in the sun. They soon find, however, that paradise comes at a price: Participation in couples therapy sessions is mandatory. What started out as a cut-rate vacation turns into an examination of the common problems many face.

The Decline of the American Empire

Four very different Montreal university teachers gather at a rambling country house to prepare a dinner. Remy (married), Claude (a homosexual), Pierre (involved with a girlfriend) and Alain (a bachelor) discuss sex, the female body and their affairs with them. Meanwhile, their four female guests, Louise (Remy's wife of 15 years), Dominique (a spinster), Diane (a divorcée) and Danielle (Pierre's girlfriend) are spending the time at a downtown health gym. They also discuss sex, the female body and, naturally, men. Later in the evening, they finally meet at the country house and have dinner. A ninth guest, named Mario, who used to know Diane, drops in on the group for some talk and has a surprise of his own.

Two Moon Junction

A young Southern débutante temporarily abandons her posh lifestyle and upcoming, semi-arranged marriage to have a lustful and erotic fling with a rugged drifter who works at a local carnival.

Starter for 10

In 1985, against the backdrop of Thatcherism, Brian Jackson enrolls in the University of Bristol, a scholarship boy from seaside Essex with a love of knowledge for its own sake and a childhood spent watching University Challenge, a college quiz show. At Bristol he tries out for the Challenge team and falls under the spell of Alice, a lovely blond with an extensive sexual past.

Hall Pass

When best buds Rick and Fred begin to show signs of restlessness at home, their wives take a bold approach to revitalize their marriages, they grant the guys a 'hall pass'—one week of freedom to do whatever they want. At first, it seems like a dream come true, but they quickly discover that their expectations of the single life—and themselves—are completely and hilariously out of sync with reality.

Helena from the Wedding

Newlyweds Alex and Alice host a New Year's Eve party for their closest friends at a remote cabin in the mountains. However, when an unexpected guest shows up, the group's facades begin to crumble.

Husbands

A common friend's sudden death brings three men, married with children, to reconsider their lives and ultimately leave together. But mindless enthusiasm for regained freedom will be short-lived.

Last Vegas

Aging pals Billy, Paddy, Archie, and Sam have been best friends since childhood. When Billy finally proposes to his much-younger girlfriend, all four friends go to Las Vegas to celebrate the end of Billy's longtime bachelorhood and relive their glory days. However, the four quickly realize that the intervening decades have changed Sin City and tested their friendship in ways they had not imagined.

Live Nude Girls

A group of old friends at a Hens Night discuss their issues, uncertainties, fears and fantasies.

She's the One

Mickey, a free-spirited New York cabbie, and Francis, a materialistic Wall Street stockbroker, are extremely competitive and confused about women as a result of their father's influence. Though they disagree about everything, they have one thing in common: Mickey's ex-fiance Heather is Francis's secret love. Though both brothers have beautiful wives, Heather triggers their longtime sibling rivalry

Kisses and Caroms

In California, Zack owns the "Breakingtime Billiards", a store that sells pool tables and game room supplies. He works with his girlfriend Jennifer; the sexy seller Tara; the installer of pool tables and best friend, the wolf David, and his idiot assistant Eddie. After having a threesome arranged by Jen with Tara, Zach breaks up his relationship with Jen, in spite of her bringing him up all the time. He tells his sexual experience to David while Jen asks for an advice to her psychologist Dr. Bob Johnson in his radio show. Along the day and after the visit of many peculiar clients, Zack concludes that Jen is his dream girl.

My Teacher's Wife

Todd Boomer is a college student aspiring to get into University. His chances are looking poor when his maths teacher, fails him in every maths test. Help arrives in the guise of the gorgeous Vicki, a mathematical genius who decides to tutor Todd. As the relationship develops,Todd finds himself in an affair with Vicki unknowing of her marriage to his math teacher.

Amateur Night

Guy Carter, an insecure expectant father unable to find work in his field, accepts a job driving hookers around Los Angeles. One long and crazy evening proves to our hero that he is, in fact, up to the task of fatherhood.

Undertaking Betty

A politician's wife and the mortician who has secretly loved her for years plan to fake her death so they can run away together.

One Hot Summer

A beautiful Cuban-American lawyer is caught in the greatest dilemma of her life stay with Ariel, her Cuban-American husband who is eager to start a family at any cost or reignite a past love with Luther, the romance of her life who unexpectedly returns to try and capture her heart once again. Set against the backdrop of one hot summer in the sultry city of Miami, this romantic comedy examines the lives and loves of Margarita Santos, a contemporary woman and her two best friends (Anabel and Viviana) as they straddle two cultures to navigate through the dilemmas they face to find love and happiness once again.

The Deal

A mother fights to save her ailing daughter after a global pandemic worse than any seen before ravaged the planet, leaving resources so scarce you must pay for them with your life.

Christmas Matchmakers

Two executive assistants scheme to get their bosses to date during the holidays, and in the process fall in love themselves.

Blue Seduction

A middle aged music composer finds himself trapped in the seductive web of a young, sexy vocalist who is looking for her own fifteen seconds of fame...

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