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Movies Like The Duchess of Cancun
Find movies like The Duchess of Cancun using TMDB similarity plus Movie Rankings community context. Our top current pick is Love Don't Co$t a Thing. Browse 18 related titles with direct links to rankings, cast pages, and matchup data.
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Love Don't Co$t a Thing
2003
A high school outcast pays a cheerleader to pose as his girlfriend so he can be considered cool.

The Best You Can
2025
Cynthia Rand is a buttoned-up New Yorker married to a brilliant professor 25 years her senior. She begins feeling the effects of her husband’s advancing age on their relationship, just as her world is turned upside down by the arrival of sharp but chronically underachieving security guard Stan Olszewski in this smart rom-com that reunites Bacon and Sedgwick on screen for the first time in 20 years.

Mumford
1999
When a would-be psychologist, curiously named Dr. Mumford, comes to the idyllic town of the same name and offers his talent for listening and a disarming frankness, the town's quirkiest citizens scramble for a seat on his couch. As he lightens hearts darkened by old secrets no one realizes he's hiding a whopper of his own, or that he's fallen head over heels for one of his patients!

The Giant Mechanical Man
2012
An offbeat romantic comedy about a silver-painted street performer and the soft spoken zoo worker who falls for him.

Mr. Right
2016
A girl falls for the "perfect" guy, who happens to have a very fatal flaw: he's a hitman on the run from the crime cartels who employ him.

Delirious
2007
Les, a small-time celebrity photographer desperate to make it big, befriends Toby, a homeless young man with no direction except a vague desire to become an actor. When by chance, Toby becomes romantically involved with K'Harma Leeds, the hottest pop star of the moment, Les grows jealous and plots revenge.

Enemies, a Love Story
1989
A ghostwriter finds himself romantically involved with his current wife, a married woman and his long-vanished wife.

Cherry
2010
Ivy League Freshman, Aaron Milton (17) gets a different kind of education when he falls for Linda (34) a vivacious former wild-child who has returned to college to straighten out her life. The curriculum gets more challenging when Aaron meets Linda's sarcastic 14 year-old daughter, Beth - who quickly develops a crush on him. The math doesn't work in either direction but the dysfunctional triangle becomes a learning experience for all involved.

The Good House
2021
Hildy Good, a wry New England realtor and descendant of the Salem witches who loves her wine and loves her secrets. Her compartmentalized life starts to unravel as she rekindles an old romance and becomes dangerously entwined in one person’s reckless behavior.

The Baltimorons
2025
A newly sober man's Christmas Eve dental emergency leads to an unexpected romance with his older dentist as they explore Baltimore together.

Cosi
1996
Lewis, a young amateur theater director, is offered a job with a governmental program for the rehabilitation of mentally ill patients in a Sydney institution. His project is overrun by one of the patients, who wants to stage the opera Cosi Fan Tutte by Mozart, despite the fact that none of the patients can sing or speak Italian. A comedy of errors ensues, but one which unifies the patients and their director in unexpected ways.

Danny Deckchair
2003
Based on a true story, the tale of a cement truck driver named Danny, whose long awaited vacation is cancelled thanks to his scheming girlfriend, Trudy. Danny escapes his grim life in suburban Australia and blasts into the skies in a chair tied with helium balloons. A mighty thunderstorm blows him clean off the map, and spits him out far away over the lush green town of Clarence. In this new town, he rockets into the world of Glenda, the town's only parking cop. While the media back home becomes obsessed with the story of his disappearance, Danny gets to reinvent himself in this new town, and in his great adventure, he discovers a true soul mate in Glenda. Fate catches up with him eventually, as Danny's true identity is revealed and Trudy--now a tabloid celebrity--comes to the idyllic town to claim Danny and drag him back to Sydney. Danny, however, is a changed man; he's discovered what it means to be happy and has found a new self-worth.

Jack Goes Boating
2010
A limo driver's blind date sparks a tale of love, betrayal, friendship and grace—centered on two working-class New York City couples.

Breaking & Exiting
2018
Harry, a charming house thief, gets more than he bargains for during an attempted burglary when he stumbles upon Daisy and decides to save her from herself, sending both of them into a darkly comedic journey of self discovery and love.

Sidewalks of New York
2001
The film follows the marital and dating lives of three men and three women who unknowingly form a tangled web of relationships. Interspersing "man on the street" interviews with scenes from the six characters' lives, the film weaves a humorous and biting commentary on the game of love -- easy to start, hard to finish.

The Elder Son
2006
A thief on the run convinces a single father that he is his long-lost son. Complications ensue when he falls in love with his newfound "sister".

Cyrus
2010
With John's social life at a standstill and his ex-wife about to get remarried, a down on his luck divorcée finally meets the woman of his dreams, only to discover she has another man in her life - her son. Before long, the two are locked in a battle of wits for the woman they both love-and it appears only one man can be left standing when it's over.

Numb
2007
Hudson Milbank is a successful Hollywood screenwriter who suddenly and strangely finds himself without any emotional feelings. He tries doctor after doctor and shrink after shrink, but nothing works. The Golf Channel, lesbian exercise classes and a dizzying variety of pills get him through the day, but don't quite solve his problem. His writing partner tries everything to get him back to normal, but it's not until Hudson meets Sara that he finds a real motivation to get better and to actually start feeling again. From the writer of Deuce Bigalow, comes NUMB, a romantic comedy following an unusual man looking for strange love.
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