Movies Like The Dilemma
If you loved The Dilemma's Comedy and Drama storytelling, these films deliver a similar experience — carefully selected for tone, themes, and emotional depth. Each pick includes where to watch it right now.
★ Top Picks
Romance & Cigarettes
Ironworker Nick lives with his wife, Kitty, and three daughters. When he meets a significantly younger woman, Tula, he starts an affair with her, much to the chagrin of his wife, and his life is thrown into upheaval. Kitty kicks Nick out of the house, and he is forced to make some difficult decisions.
Butterfly on a Wheel
A sociopathic kidnapper methodically pushes a desperate pair of parents to their absolute breaking point.
Heartburn
She's a magazine writer who gives up her career for love and family. He's a playboy newspaper columnist who can't quite give up his old tricks. And if that combination doesn't give a relationship heartburn, nothing will.
A Guy Thing
Paul Morse is a good guy. When his friends throw him a wild bachelor party, he just wants to keep his conscience clean -- which is why he's shocked when he wakes up in bed with a beautiful girl named Becky and can't remember the night before. Desperate to keep his fiancée, Karen, from finding out what may or may not be the truth, he tells her a teensy lie. Soon his lies are spiraling out of control and his life is a series of comical misunderstandings.
What Doesn't Kill You
Two childhood friends from South Boston turn to crime as a way to get by, ultimately causing a strain in their personal lives and their friendship.
On the Rocks
Faced with sudden doubts about her marriage, a young New York mother teams up with her larger-than-life playboy father to tail her husband.
Careful What You Wish For
A guy gets more than he bargained for after entering into an affair with the wife of an investment banker. Soon, a suspicious death and substantial life insurance policy embroil him in a scandal.
Lawn Dogs
In the affluent, gated community of Camelot Gardens, bored wives indiscriminately sleep around while their unwitting husbands try desperately to climb the social ladder. Trent, a 21-year-old outsider who mows the neighborhood lawns, quietly observes the infidelities and hypocrisies of this overly privileged society. When Devon, a 10-year-old daughter from one family, forges a friendship with Trent, things suddenly get very complicated.
More Movies Like The Dilemma
Friendship
Suburban dad Craig falls hard for his charismatic new neighbor Austin, and his attempts to make an adult male friend threatens to ruin both of their lives.
Last Night
Michael and Joanna are a young and successful married couple who appear to have it all. But when Michael finds himself alone on a business trip with an attractive new colleague and Joanna encounters the other great love of her life, each is thrust into an evening of temptation.
Extract
The owner of a factory that produces flavor extracts, Joel Reynold seems to have it all, but really doesn't. What's missing is sexual attention from his wife, Suzie. Joel hatches a convoluted plan to get Suzie to cheat on him, thereby clearing the way for Joel to have an affair with Cindy, an employee. But what Joel doesn't know is that Cindy is a sociopathic con artist, and a freak workplace accident clears the way for her to ruin Joel forever.
Before We Go
A woman who is robbed on her way to catch the 1:30 train to Boston is left stranded in New York City. She meets a man who helps her during the course of the night and the two form a romance.
The Daytrippers
Eliza D'Amico thinks her marriage to Louis is going great until she finds a mysterious love note to her husband. Concerned, she goes to her mother for advice. Eliza, her parents, her sister Jo, and Jo's boyfriend all pile into the station wagon and go to the city to confront Louis with the letter. On the way, the five explore their relations with each other and meet many interesting people.
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.
State of the Union
An industrialist is urged to run for President, but this requires uncomfortable compromises on both political and marital levels.
He's Just Not That Into You
Have you ever wondered why they said they would call but didn't, or why they don't want to sleep with you anymore, or why your relationship isn't going to the next level? Maybe they're just not that into you. Gigi wants a man who says he'll call her - and actually does - while Alex advises her to stop waiting by the phone. Beth wants a proposal after years of a committed relationship with her boyfriend, Neil, who is just fine with the way things are. Janine's not sure if she can trust her husband, Ben, who can't quite trust himself around Anna. Anna can't decide between the sexy married guy or her straightforward, no-sparks standby, Conor, who can't get over the fact that he can't have her. And Mary, who's found an entire network of loving, supportive men, just needs to find one who's straight.
Diary of a Mad Housewife
Tina Balser is a bored New York housewife-mother married to Jonathan, a pompous, social-climbing lawyer who ridicules her in front of their children, criticizing everything she does or wears. She begins an affair with George Prager, a dashing, successful, and blatantly sadistic writer.
The Good Girl
A discount store clerk strikes up an affair with a stock boy who considers himself the incarnation of Holden Caulfield.
Alfie
A tale of a philosophical womanizer who is forced to question his seemingly carefree existence.
Sleeping with Other People
Can two serial cheaters get a second chance at love? After a one-night stand in college, New Yorkers Lainey and Jake meet by chance twelve years later and discover they each have the same problem: because of their monogamy-challenged ways, neither can maintain a relationship. Determined to stay friends despite their mutual attraction, they make a pact to keep it platonic, a deal that proves easier said than done.
Why These Movies Are Similar
These recommendations share core qualities with The Dilemma (2011): Comedy and Drama themes, similar narrative structure, and comparable emotional depth. NoBadPicks uses a combination of TMDB collaborative filtering, genre matching, and AI analysis to surface films most likely to resonate with fans of The Dilemma.
See full details for The Dilemma (2011)