This film offers a slightly different take on the romantic comedy, focusing on the messy aftermath of a relationship ending.

Vince Vaughn and Jennifer Aniston play a couple who break up but are forced to continue living together in their condo, leading to passive-aggressive warfare and unexpected moments. While it has romantic elements and humor, its core theme of separation makes it less of a direct match for the hopeful romantic journey in Leap Year.

Location detail: The condo shared by the characters is a significant part of the film's setting and conflict, almost acting as a third character.

A battle-of-the-sexes rom-com starring Katherine Heigl as a relationship-challenged TV producer and Gerard Butler as a chauvinistic TV personality she's forced to work with.

His cynical 'ugly truth' about relationships clashes with her romantic ideals, leading to a series of tests and, predictably, unexpected attraction. It's a witty, fast-paced rom-com, though it's more urban and less travel-focused than Leap Year.

Trivia: The film was directed by Robert Luketic, who also directed 'Legally Blonde' and '21'.

This film delves into the complications of love and friendship when a woman (Ginnifer Goodwin) falls for her best friend's fiancé.

It's a relationship-focused rom-com exploring difficult choices and unexpected feelings. While it lacks the travel element of Leap Year, it offers a look at romantic complications and finding love in unexpected places, albeit with more dramatic undertones.

Casting note: Kate Hudson, who stars as the best friend, also served as a producer on the film.

An iconic British rom-com following a single woman (Renée Zellweger) chronicling her life and romantic entanglements in a diary.

While grounded in London and less about travel than Leap Year, it's a beloved entry in the genre, celebrated for its relatable protagonist and charming love triangle (Hugh Grant and Colin Firth). It captures the humor and awkwardness of navigating modern relationships.

Fun fact: Renée Zellweger famously gained weight and worked on her British accent for the role, completely immersing herself in the character.

This film centers on a woman (Katherine Heigl) who has been a bridesmaid 27 times but struggles to find her own love story.

Her journey involves navigating relationships and finally putting herself first. While not a travel film, it shares the sweet, hopeful romantic comedy tone of Leap Year and features a charming dynamic between the leads (Heigl and James Marsden) as they initially clash before falling for each other.

Behind the scenes: The montage showing Jane's 27 different bridesmaid dresses was a fan favorite and required extensive costume work to create such a wide variety of often outlandish gowns.

A classic early 2000s rom-com starring Jennifer Lopez as a meticulous wedding planner who falls for the groom of one of her biggest clients (Matthew McConaughey).

Like Leap Year, it features a charming leading man and a focus on romantic hurdles. While less about travel, it's full of the genre's signature charm, witty banter, and romantic complications as the characters navigate a tricky situation.

Did you know? This was the first film where Jennifer Lopez received a salary of over one million dollars.

This film features travel to an iconic destination (Las Vegas) and a plot built on forced proximity, much like the core dynamic in Leap Year.

Cameron Diaz and Ashton Kutcher play strangers who meet in Vegas, get married during a wild night, and then win a huge jackpot. A judge orders them to live together for six months to prove their marriage is legitimate before they can divorce and split the money, leading to comedy and unexpected romance.

Location detail: While set in Las Vegas, many scenes were filmed on soundstages to control the environment, but they captured the city's atmosphere effectively.

For a high-energy rom-com with fantastic lead chemistry, look no further than How to Lose a Guy in 10 Days. While not a travel movie like Leap Year, it features a fun, high-concept premise and a central couple you root for.

Matthew McConaughey plays an advertising exec who bets he can make any woman fall in love with him in 10 days. Kate Hudson plays a journalist writing an article on how to lose a guy in 10 days. Their opposing goals lead to hilarious and unexpected romantic entanglements.

Interesting fact: The iconic yellow dress Kate Hudson wears in the finale was custom-made by designer Dina Bar-El and has become synonymous with the film.

If you enjoy the theme of fate bringing people together, Serendipity is a charming watch. While less about a specific travel quest than Leap Year, it follows two people who meet by chance and decide to let destiny guide them back to each other.

John Cusack and Kate Beckinsale star as strangers who share a magical night in New York City and then separate, believing fate will reunite them if they are meant to be together. Years later, both are engaged to others but can't shake the feeling they should find each other again.

Behind the scenes: The famous Bloomingdale's department store scene is central to the plot, where the characters first exchange contact information in a book.

Set partly in Ireland, P.S. I Love You shares a geographical link with Leap Year and explores a journey of love and self-discovery tied to a specific place.

Hilary Swank plays a young widow who receives a series of letters from her late husband (Gerard Butler), designed to help her move on. One of the letters sends her on a trip to his homeland, Ireland, where she reconnects with his past and begins to embrace her future.

Trivia: The movie features several prominent Irish actors in supporting roles, adding to its authentic feel, and the scenes in Ireland showcase the country's beautiful landscapes.

Trade places and find romance across continents in The Holiday! This film features two women from different countries (Cameron Diaz from LA, Kate Winslet from London) who swap homes for the holidays to escape their relationship troubles.

Their change of scenery leads them both to meet charming local guys (Jude Law and Jack Black). It's a sweet story about fresh starts and falling in love when you least expect it, much like the journey in Leap Year.

Production detail: The quaint English cottage shown in the film wasn't a real house; it was actually built from scratch in a field specifically for the movie's production.

Escape to Italy in Under the Tuscan Sun! While less about a specific proposal quest than Leap Year, this film shares the theme of an American woman finding unexpected romance and life changes while traveling abroad.

Diane Lane stars as a writer who impulsively buys a villa in Tuscany after her divorce. As she rebuilds her life and home, she finds new friendships and the possibility of love amidst the stunning Italian scenery. It's a beautiful story about second chances and embracing the unexpected.

Interesting tidbit: The film is based on Frances Mayes' best-selling memoir, although the movie takes significant liberties with the story, adding more romantic elements.

Journey to the romantic landscapes of Italy with Letters to Juliet! Like Leap Year, this film uses a beautiful foreign setting as the backdrop for a search for love.

Amanda Seyfried plays a young American who discovers a group of women in Verona who answer letters left for Shakespeare's Juliet. She finds an old letter and sets out to help the writer find her lost love, embarking on a charming road trip through the Italian countryside with the writer's skeptical grandson.

Did you know? Verona truly has 'Secretaries of Juliet' who respond to letters addressed to the character, a tradition that dates back decades and inspired the film's premise.

If you loved the 'proposal while traveling' hook and the dynamic between city meets country in Leap Year, The Proposal delivers similar delightful sparks!

Sandra Bullock plays a high-powered editor facing deportation who forces her assistant (Ryan Reynolds) to marry her. They travel to Alaska to meet his quirky family, leading to hilarious situations and unexpected feelings. The chemistry between Bullock and Reynolds is off the charts, making their forced proximity journey truly electric.

Fun fact: The iconic scene where Bullock and Reynolds dance around a campfire was largely improvised, showcasing their fantastic comedic timing.