Top 20 Best Romance Movies of the 2000s

While many Adam Sandler films are silly, they also have heart. “50 First Dates” is one of the best examples of this blend with the inclusion of a fun premise. Henry Roth wants to date Lucy Whitmore, but then he realizes the latter’s amnesia makes their relationship complicated. Sandler’s character then becomes a much better person as he wins Drew Barrymore’s love interest back every day. There’s an undeniable sweetness here as Roth tries everything to proclaim his love for Whitmore. Using the romantic setting of Hawaii, this movie makes you believe again in a relationship that defies the odds.

While her parents are divorcing, Maya Hayes asks about how they met. This creates the setup for “Definitely, Maybe,” a movie full of twists, humor, and lots of romance. Ryan Reynolds plays the dad who recounts his past relationships while seeing if his kid can guess the mother’s identity. Abigail Breslin plays Maya, bringing a precocious energy and playing well off of the always-reliable Reynolds. There’s also an impressive cast of potential moms that include Elizabeth Banks, Isla Fisher, and Rachel Weisz. It’s also an endearing film about the bond between dads and daughters. Before it’s all over, the likable characters give you the sense that Will’s love story is far from over.

If you’ve ever thought about luck in relationships, “Serendipity” puts the idea to the ultimate test. Sara meets Jonathan and later tells him about how she lets fate dictate her love life. This sets up an entertaining plot, with the two characters testing if their partnership can last through elevator rides and other strange events. John Cusack and Kate Beckinsale bring a vibrant energy to their roles, with an ability to play authentic people desperate to find love. Their leads find themselves in surprising situations that eventually bring them back together. Whether or not you believe in the title phrase, this movie does have an unmistakable magic to it.

Taking a trip to Spain, Vicky and Cristina fall under the spell of the charismatic Juan Antonio Gonzalo. The man woos each woman while working through a complex relationship with his ex-wife María Elena. Writer and director Woody Allen crafts a messy love story, full of double-crosses and secret affairs. You could make an argument that the beautiful and talented cast is worth the price of admission. While that might be true, the movie also features plenty of romance and comedy that makes for an entertaining soap opera. There’s also Penélope Cruz’s Oscar-winning performance to round out a chaotic plot.

In a career-altering performance, Adam Sandler shows he’s much more than a goofy “SNL” alum. He plays a tightly wound character named Barry who’s harboring both childlike wonder and primal rage. The businessman juggles family troubles, extortion, and a fledgling romance with Lena Leonard. This doesn’t even include his frequent-flier-miles scheme that lets him chase Leonard to Hawaii. It’s not your average rom-com in any way, making for several unexpected scenes that include confrontations with Philip Seymour Hoffman’s Dean. Paul Thomas Anderson’s superb direction brings this all together, letting Sandler’s brilliant work shine opposite the charming work of Emily Watson.

Starring John Cusack, this 2000 rom-com takes an authentic and sometimes uncomfortable look at relationships. The lead character Rob Gordon re-examines his life after a breakup by examining the concept of romance. Cusack’s performance grounds the film while letting the natural humor of it all come out. “High Fidelity” is for music lovers, but it’s also for people who have survived relationships with music lovers. It features the universal feeling of uncertainty over yourself, your romantic skills, and your past partnerships. The project even features a killer Marvin Gaye cover by Jack Black. Through it all, we come to care for the lead guy through all his faults.

For any fans of this film, the title alone might make you cry. “A Walk to Remember” features a tragic romance full of inspiring moments. The Nicholas Sparks adaptation follows the love story between Landon Carter and Jamie Sullivan. It’s a classic tale of opposites attract, one being a bad boy and the other being a much more traditional girl. This doesn’t stop them from coming together as their different perspectives fuel a compelling plot. Despite Sullivan’s cancer diagnosis, the two prove their bond can’t be shaken. The heartbreaking narrative features all the highs and lows of teenage relationships.

Toula Portokalos just wants to find love, but she’s thirty and single. This brings out disapproval from her family and fuels a hilarious rom-com. “My Big Fat Greek Wedding” is full of many culture clashes between the Portokalos family and their potential in-laws. The main character falls for Ian Miller, welcoming him into her crazy life with traditions and cultural nuances to learn. It’s a movie full of all the family drama, awkwardness, and romance that’s universal regardless of your ethnicity. The witty script also lets this fairytale have a healthy dose of memorable lines and catchphrases.

In this 1960s-set Hong Kong romance, two people find themselves in a strange predicament. They fall in love after finding out their partners are seeing each other. Wong Kar-wai’s timeless drama features stellar lead performances from Maggie Cheung and Tony Leung. Along the way, both Chow Mo-wan and Su Li-zhen contemplate their potential future together. Their tragic story might feature a fairytale payoff, but it does set up an open ending that asks viewers to contemplate their own lives. The director’s singular directing style creates an unforgettable mood and a deeply romantic experience.

With the central trio of cast members, “Bridget Jones’s Diary” is a classic romance in every sense. Renée Zellweger plays this part perfectly, giving the character a relatable and comic edge. She plays the publicity assistant who writes in her diary and can’t stop pining over two men. The latter duo happens to be the incredible Colin Firth and Hugh Grant. Along the way, audiences are treated to an engaging love triangle that’s full of great banter. Zellweger is at the top of her game, with an impressive accent and bubbly energy that you can’t help but love. The title role and concept were so successful that they brought the actress back for multiple sequels.

In most romantic films, the action is centered on two – maybe three – people and the various trials and tribulations that go along with falling head over heels. This British rom-com turns things up a notch, focusing on ten different stories that have one thing in common: love. Set in London five weeks before Christmas, this film follows a rock n’ roller, a couple of adult film stars, a sexually frustrated graphic designer, and even the Prime Minister. They, along with an array of other characters, suffer through the ups and downs of searching for, finding, and holding onto loved ones. Teeming with endless wit and warmth to match, “Love Actually” reminds us that love is all you need.

Do you ever feel like an aging movie star falling in love with a much younger married woman during a business trip to Tokyo? Okay, neither do we, but it is the premise of this film from the early 2000s. When Bob begins to fall for Charlotte during his time in Tokyo, it becomes clear that their relationship has an expiration date. Set to the backdrop of jazzy hotel bars and the exciting nightlife of a city caught in a non-stop bustle, this film is really about spontaneous relationships and how we handle them. Beautifully scripted and shot to perfection by Sofia Coppola, you’ll be booking the next flight to Japan to chase down love after seeing this film.

Have you ever broken up with someone and wished that you could erase all memory of him or her from your mind? This film takes that premise and uses it to create a world where deleting bad memories from your brain is on par with a trip to the dentist. Joel is thrilled when he meets a woman during an impulsive trip to the beach. There is only one problem: has he met her before? This love story is about as unconventional as they come. The off-the-wall writing and the mind-bending sets are paired perfectly with the warmth put forward by the two main characters. Definitely a weird one, it’s sure to make you reexamine some of your past relationships.

Don’t be deterred by the subtitles! This beautiful and quirky flick is overflowing with moments that will stick with you long after the credits have rolled. When timid Parisian waitress Amélie makes a concerted effort to improve the lives of those around her, she quickly discovers that her own happiness is diminishing. From there, she decides to pursue an eccentric man prone to collecting photographs. As the story unfolds, it becomes clear that love is a two-way street and one must give as much as one takes. A critical and commercial success, this film reminded audiences that love is all around us, and to see it you must simply open your eyes.

Is Joseph Gordon-Levitt the John Cusack of today? It sure feels like it during this unique love story. This film takes a fresh approach to a tired genre and is chock-full of moments sure to make you smile. When hopeless romantic Tom falls for the titular Summer, things don’t go exactly as planned for either of them. The film takes us on a journey through the 500 days of their relationship, jumping from moment to moment to give audiences a well-rounded view of the characters’ time together. At its heart, this romantic flick is about the struggles we all go through when falling in love.

When a passionate connection emerges between two people, it simply cannot be ignored. In the summer of 1963, two cowboys fall in love while herding sheep through the Wyoming mountains. As their lives move in different directions, the two men struggle to balance their affair with their respective marriages. This film is an intimate look into the lives of a two men brought together by love, but kept apart by society. Filled with an array of tender moments that are brilliantly juxtaposed with the wild and untamed nature of the landscape, this love story truly stood out when it was first released, and still stands as a great romance flick today.

She may have died almost 200 years ago, but Jane Austen is still making the world tear up with her works of romantic fiction. Adapted for audiences in the mid-2000s, this film follows Elizabeth Bennet as she falls in love with the reserved upper-class gentleman, Mr. Darcy. While he initially spurns her advances, Mr. Darcy soon comes to appreciate Elizabeth – with a deep passion burning inside them both. This period piece is filled with universal themes that are sure to connect with even the staunchest of critics. And if historical British romances are your thing, don’t forget to check out “Atonement” - plenty of Keira Knightley in that one, too.

There wasn’t a dry eye in the house when this romance first graced the silver screen. Based on the novel by swoon-inducing writer Nicholas Sparks, this film was the go-to date movie for the mid-2000s teenager. Taking place in South Carolina in the 1940s, working-class Noah falls hard for Allie, a girl who hails from a family of wealth and privilege. While society attempts to keep them apart, their love slowly blossoms from teenage lust to passionate romance. Filled with tender moments that will inspire both the hopelessly romantic and the stoically reserved, this film is sure to leave you reaching for the tissues.

Overflowing with style and packed to the gills with raw sexuality, this classic has more than enough romance to go around. Set in turn of the century Paris and centered on the exploits of the infamous Moulin Rouge cabaret, a young poet falls hard for the club’s most provocative dancer. Brought to life through the mad genius of Australian director Baz Luhrmann, this film pays homage to a high-flying time of eccentric parties and declarations of love that has since passed us by. Playing the roles of star-crossed lovers to perfection, Ewan McGregor and Nicole Kidman ooze romance from start to finish. Earning wide acclaim, this film had many yearning for a fling in the city of lights.

Taking place nine years after the events of its 1995 predecessor, this film once again follows Jesse and Céline as they walk the streets of a beautiful European city while discussing life, love, sex, and the cultural differences that define them. The film feels less like a sequel and more like a chance encounter with an old friend – sprinkled with moments of innocent flirtation, melancholic memories, and hope for the future. Simplistic in its style, “Before Sunset” is overflowing in intimacy, with the connection between the two protagonists pushing and pulling the narrative forward. While the film operates as a realistic portrayal of a fantastical situation, the strong writing and impassioned performances make it a romance for the ages.

Did we forget another classic romance from the 2000s? Let us know in the comments below.