14 2000s Rom-Coms That Hold Up Surprisingly Well

The romantic comedies of the 2000s are unforgettable. They provided a mix of humor, charm, and romance that is still appreciated today. While trends have come and gone, these films continue to entertain audiences of all ages. Whether it is the quirky characters or the heartwarming stories, they have something that makes them stand the test of time. Join us as we revisit these iconic rom-coms.

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Love Actually (2003)

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This British ensemble film explores different love stories during the holiday season. The interwoven plotlines of family, friendship, and romance make it relatable and endearing. With a star-studded cast including Hugh Grant, Emma Thompson, and Colin Firth, Love Actually combines humor and heartfelt moments. Its holiday setting adds to its timeless charm, making it perfect for any season.

The movie’s exploration of love in all its forms, from familial to romantic, feels genuine and warm. Despite its age, Love Actually holds up due to its heartwarming moments and witty script. The blend of touching and funny scenes has ensured its place as a favorite. The film remains a beloved classic, thanks to its emotional resonance and star power.

The Proposal (2009)

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Starring Sandra Bullock and Ryan Reynolds, The Proposal is a story about an unlikely romance between a tough editor and her assistant. The movie is full of laughs, with sharp dialogue and funny scenarios that keep the pace lively. Bullock’s comedic timing paired with Reynolds’ charm makes for a dynamic and entertaining duo. Their chemistry adds a genuine layer to the story of forced proximity and unexpected love.

The setting, with its Alaskan backdrop, gives the film a refreshing change from typical rom-com locations. The balance of humor, romance, and quirky characters ensures that the movie remains engaging. Though released near the end of the decade, The Proposal still feels like a standout entry. Its combination of heartfelt moments and laughter has kept it relevant.

13 Going on 30 (2004)

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This movie is a delightful fantasy that follows a 13-year-old girl who magically wakes up as a 30-year-old woman. Jennifer Garner’s performance as the childlike adult is both charming and relatable, offering a look at growing up and balancing dreams with reality. The movie explores themes of friendship, self-identity, and learning from the past. Its quirky tone and heartfelt moments have allowed it to remain beloved by fans.

The film’s nostalgic element, especially the 80s references, adds to its charm. It is more than just a rom-com, as it is a coming-of-age story with universal themes. The magical twist makes the story feel lighthearted while still exploring deeper emotions. 13 Going on 30 has retained its appeal over the years, with its blend of humor and heartfelt moments.

Sweet Home Alabama (2002)

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In this Southern-set rom-com, Reese Witherspoon stars as a successful fashion designer who must return home to finalize her divorce. The film combines humor with heartfelt moments as Witherspoon’s character faces her past and her future. The quirky Southern setting provides a refreshing backdrop to the romantic conflict between her old love and her new life. The cast, including Josh Lucas and Patrick Dempsey, brings great energy to the story.

The movie’s exploration of self-discovery and second chances resonates with many viewers. Sweet Home Alabama remains charming due to its mix of humor, romance, and Southern charm. The story is both lighthearted and touching, offering something for both romantic and comedy fans. Witherspoon’s performance helps the movie hold up as one of the best rom-coms of the early 2000s.

How to Lose a Guy in 10 Days (2003)

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Kate Hudson and Matthew McConaughey star in this playful film about a woman who tries to push a man away while he attempts to make her fall in love with him. The film is a fun take on romantic misunderstandings and opposites attracting. Hudson’s comedic timing and McConaughey’s charm make their chemistry undeniable. The plot’s premise is simple but filled with enough humor and twists to keep things engaging.

What makes this rom-com hold up is its mix of humor, likable characters, and fun premise. The scenes are memorable, with the two leads creating a dynamic that works well. The plot may seem familiar, but its execution makes it stand out among other rom-coms. How to Lose a Guy in 10 Days remains one of the top films to revisit for a light and enjoyable watch.

My Big Fat Greek Wedding (2002)

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This charming story about a Greek woman who falls in love with a non-Greek man explores cultural clashes, family dynamics, and the importance of love and acceptance. The film’s humor is grounded in the relatable struggles of family and tradition. Nia Vardalos, who also wrote the script, stars in the lead role, making her character both relatable and endearing. The film’s heartwarming story helped it become one of the highest-grossing romantic comedies of all time.

The film’s themes of family loyalty and personal growth resonate deeply with viewers. My Big Fat Greek Wedding balances humor with heart in a way that feels both fresh and timeless. The quirky characters and hilarious moments make it a standout in the rom-com genre. Its universal appeal continues to make it a favorite, even years after its release.

The Wedding Planner (2001)

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Starring Jennifer Lopez and Matthew McConaughey, The Wedding Planner offers a fun, romantic story about a wedding planner who falls in love with the groom of one of her clients. The chemistry between the leads drives the film, with Lopez’s charm and McConaughey’s easygoing style making their romance believable. The film is filled with humor, love, and the typical chaos that surrounds wedding planning. Its relatable storyline of love at first sight continues to connect with audiences.

The movie stands out due to its mixture of lighthearted comedy and the deeper theme of finding love in unexpected places. Lopez’s role as a successful, independent woman adds a refreshing layer to the typical rom-com protagonist. The blend of humor, romance, and wedding chaos makes it one of the more enjoyable films of the early 2000s. It remains a fan favorite due to its charming leads and fun premise.

Legally Blonde (2001)

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In this iconic film, Reese Witherspoon stars as Elle Woods, a sorority girl who enrolls in Harvard Law School to win back her ex-boyfriend, only to find her true calling. The film’s humor and message of empowerment resonate with audiences of all ages. Witherspoon’s portrayal of Elle’s transformation from a fashion-obsessed student to a determined lawyer remains both entertaining and inspiring. The movie’s blend of humor, heart, and girl power has ensured its lasting appeal.

What makes Legally Blonde a standout is its uplifting message about defying expectations and following your dreams. Elle’s journey shows that intelligence and beauty are not mutually exclusive, a refreshing take on traditional rom-com tropes. The film remains popular due to its humor, wit, and Reese Witherspoon’s charismatic performance. It has become a cultural touchstone for many rom-com lovers.

The Princess Diaries (2001)

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Anne Hathaway stars as Mia Thermopolis, a teenager who discovers she is heir to the throne of a small European country. This coming-of-age story blends humor, romance, and a fairytale twist. Mia’s journey of self-discovery, with help from her grandmother (played by Julie Andrews), makes it both entertaining and heartwarming. The film’s messages about embracing who you are and growing into yourself have a timeless appeal.

The movie’s mix of teen angst, royal life, and the pursuit of love make it a fun and relatable watch. Hathaway’s performance helped establish her as a major star, while Andrews brought warmth and wisdom to the film. The Princess Diaries remains a beloved rom-com for fans of all ages. Its charm and positive messages have made it a go-to film for rewatching.

The 40-Year-Old Virgin (2005)

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Steve Carell stars in this hilarious film as a middle-aged man who has never had a romantic relationship. The film mixes awkward humor with heartfelt moments as he navigates his personal life. The ensemble cast, including Paul Rudd and Seth Rogen, adds to the comedic charm, making each scene unforgettable. The movie’s blend of raw humor and emotional growth makes it a standout in the rom-com genre.

What sets The 40-Year-Old Virgin apart is its ability to tackle awkward situations with both humor and sensitivity. Carell’s performance, along with the witty script, makes the movie a modern classic. The film explores themes of vulnerability, love, and friendship, while still keeping things lighthearted. It has remained a fan favorite due to its timeless humor and unforgettable moments.

Kate & Leopold (2001)

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Hugh Jackman and Meg Ryan star in this charming film about a 19th-century Duke who time-travels to the 21st century, where he meets Ryan’s character. The mix of historical romance and modern-day humor gives the film a unique appeal. The chemistry between Jackman and Ryan creates a believable love story that crosses centuries. Their performances elevate the film, making it more than just another time-travel story.

Kate & Leopold holds up because of its timeless themes of love and destiny. Jackman’s portrayal of the charming Duke adds a touch of elegance to the movie, while Ryan’s relatable character makes her journey feel authentic. The film’s blend of humor and romance, with a bit of fantasy, ensures it remains enjoyable for a wide audience. Its warmth and wit continue to make it a standout rom-com.

Failure to Launch (2006)

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This romantic comedy stars Matthew McConaughey as a 35-year-old man still living with his parents, with Sarah Jessica Parker as the woman hired to help him move out. The movie’s premise is both quirky and relatable, with McConaughey’s charm and Parker’s wit driving the story forward. The supporting cast, including Kathy Bates and Terry Bradshaw, adds a fun dynamic to the film. It’s a light-hearted look at relationships, independence, and growing up.

Failure to Launch holds up due to its entertaining storyline and strong performances. The characters’ personal growth throughout the film adds a meaningful layer to the rom-com, making it more than just fluff. The humor is relatable, especially for those who have had to deal with the challenges of becoming independent. McConaughey and Parker’s chemistry keeps the film engaging and fun to watch.

Just Like Heaven (2005)

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Reese Witherspoon and Mark Ruffalo star in this charming rom-com about a woman who, after a car accident, haunts her apartment and forms an unexpected bond with the new tenant. The film combines elements of romance and supernatural intrigue, creating a unique and refreshing story. Witherspoon and Ruffalo’s performances are endearing, adding warmth to the film’s otherwise lighthearted plot. Their chemistry makes the film a sweet, enjoyable watch.

The blend of supernatural elements with romantic comedy is what makes Just Like Heaven stand out. The film’s ability to mix humor with emotional depth gives it a timeless quality. It tackles themes of love, life after loss, and the importance of letting go, making it feel fresh even years after its release. The movie’s heartwarming message and lovable characters ensure it holds up well today.

Serendipity (2001)

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Serendipity follows the story of Jonathan and Sara, two strangers who meet by chance and leave their future together up to fate. The film’s mix of romance, comedy, and a touch of magic makes it a timeless classic. John Cusack and Kate Beckinsale bring depth to their roles, with their chemistry adding warmth to the story. The film’s charming New York setting and its theme of destiny have kept it a favorite over the years.

The idea of love guided by fate is one that continues to resonate with audiences, and Serendipity does it beautifully. The movie’s ability to mix whimsy with heart is one of the reasons it remains so beloved. Its exploration of chance encounters and missed opportunities gives it a nostalgic feel. Fans of romantic comedies continue to appreciate the film for its heartfelt moments and lighthearted charm.

This article originally appeared on Avocadu.