The Best Romantic Comedies Of The 2000s, Ranked By Fans

Ranker Film

Updated June 3, 2024 79.7K views 70 items

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Vote up your favorite rom-coms released between 2000 and 2009.

Nostalgia pairs well with love and laughter, especially when it comes to the best 2000s rom-coms. The early aughts were a golden era for the romantic comedy genre, offering a delightful mix of heartwarming and hilarious tales that have become classics. Movie enthusiasts have come together to rank these gems, from the charming misadventures to the quirky quests for love that defined a decade.

Film aficionados will recall the 2000s as a time when the rom-com reigned supreme, with stories that often depicted endearing characters who were wonderfully imperfect or searching for affection in the least likely places. This list spans the spectrum, featuring everything from feel-good flicks that became box office hits to cult favorites that garnered a dedicated following.

What made these 2000s rom coms truly the best? Take early 2000s rom com, How to Lose a Guy in 10 Days, for example. It perfectly encapsulates the archetypal battle of the sexes plot with electric chemistry between Kate Hudson and Matthew McConaughey, and satirizes modern dating woes with hilarious missteps while still delivering heartwarming insights into relationships.

Or Legally Blonde, which transcends being just another college comedy by imbuing depth to its lovable heroine Elle Woods, played by Reese Witherspoon. It's an empowering underdog story wrapped in pink comedic flair. Or hits like The Proposal, which puts a fresh spin on the classic fake relationship trope, anchored by Sandra Bullock and Ryan Reynolds. With whip-smart dialogue exploring workplace dynamics, it blends laughs and heart effortlessly. These movies strike that perfect balance of humor and heart that romantic comedy fans crave. With likable leads, clever writing, and indelible pop culture moments, they exemplify why the 2000s remains a beloved decade for this comforting yet insightful genre.

It's time to weigh in on which movie hits the sweet spot of romance and comedy. Do the feel-good narratives still warm the heart? Does the comedic timing still elicit belly laughs? Upvote the best films and join the conversation to reminisce about why these best 2000s rom-coms made that decade one of the most memorable in the history of romantic comedies.

Most divisive: What Women Want

Over 2.2K Ranker voters have come together to rank this list of The Best Romantic Comedies Of The 2000s, Ranked By Fans

1
How to Lose a Guy in 10 Days
Kate Hudson, Matthew McConaughey, Adam Goldberg
987 votes
How to Lose a Guy in 10 Days delivers an amusing war-of-the-sexes battle stacked with irresistible chemistry between leads - Kate Hudson and Matthew McConaughey. Directed by Donald Petrie, it revolves around Andie Anderson (Hudson), a journalist tasked with writing an article about driving away men using various tactics. She chooses advertising executive Benjamin Barry (McConaughey), unknowing that he has wagered his own bet involving dating women. This light-hearted romantic comedy captured audiences with its wacky premise while showcasing poignant insights into relationships.
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2
The Proposal
Sandra Bullock, Ryan Reynolds, Mary Steenburgen
845 votes
The Proposal provides a delightful take on the classic fake relationship trope with two powerhouse actors, Sandra Bullock and Ryan Reynolds, leading the charge. The film follows a Canadian executive who convinces her overworked assistant to marry her in order to avoid deportation. Directed by Anne Fletcher, this sophisticated comedy deftly explores themes of power dynamics, vulnerability, and love in unexpected places. It received praise for sharp dialogue and contributed memorable moments to pop culture, like Bullock's dance scene with Betty White.
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3
Legally Blonde
Reese Witherspoon, Luke Wilson, Selma Blair
679 votes
Legally Blonde turned Reese Witherspoon into America’s sweetheart when she portrayed sorority queen Elle Woods seeking justice by storming Harvard Law School after being dumped by her boyfriend Warner Huntington III (Matthew Davis). Director Robert Luketic successfully created an empowering story of self-discovery that challenges stereotypes about beauty versus intellect. The film's legacy includes a successful musical adaptation on Broadway and a much-awaited upcoming third installment, proving that persistence pays off.
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4
The Princess Diaries
Julie Andrews, Anne Hathaway, Héctor Elizondo
455 votes
The Princess Diaries catapulted Anne Hathaway into stardom as she starred alongside Julie Andrews in this charming Cinderella-esque tale directed by Garry Marshall. Based on Meg Cabot's best-selling novel series, the story follows a nerdy high school girl named Mia Thermopolis who discovers she is heir apparent to the Genovian throne. Showcasing themes of empowerment and acceptance amidst royal responsibilities and societal expectations, The Princess Diaries was nominated for numerous awards — earning recognition for supporting performances from Heather Matarazzo and Hector Elizondo.
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5
13 Going on 30
Jennifer Garner, Mark Ruffalo, Judy Greer
466 votes
In 13 Going on 30, Jennifer Garner masterfully plays Jenna Rink – an adolescent who wishes to grow up overnight but grapples with the ramifications of her life choices. Mark Ruffalo stars opposite as the supportive best friend Matt, lending his charm and down-to-earth demeanor to counterbalance Jenna's chaotic journey. Directed by Gary Winick, this touching fantasy-comedy reminds viewers about the importance of authentic connections while aging gracefully.
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6
Miss Congeniality
Sandra Bullock, Michael Caine, Benjamin Bratt
500 votes
Miss Congeniality showcases Sandra Bullock's knack for transforming unique characters into relatable personas: talent visible through her portrayal of Gracie Hart – a tomboyish FBI agent assigned to go undercover in a beauty pageant. Expertly led by director Donald Petrie, the movie offers rib-tickling humor and a sizzling dynamic between Bullock and love interest Benjamin Bratt. It also features a memorable performance from Michael Caine as Gracie's pageant coach, propelling the film to cult status in the rom-com repertoire.
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7
27 Dresses
Katherine Heigl, James Marsden, Malin Akerman
448 votes
27 Dresses marks Katheine Heigl’s transition into romantic lead territory as she successfully portrays Jane Nichols - a chronic bridesmaid who supports her sister's wedding plans despite harboring secret feelings for the groom-to-be (Edward Burns). Entrusted with writing columns documenting their romance is Kevin Doyle (James Marsden), whose alter ego is a pessimistic wedding reporter. Directed by Anne Fletcher, this heartwarming film narrates Jane's efforts to make others happy while learning how to commit when love is reciprocated.
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8
She's the Man
Amanda Bynes, James Kirk, Channing Tatum
418 votes
She’s the Man is a delightful modern retelling of William Shakespeare’s “Twelfth Night”, pulling in Amanda Bynes' comic genius as Viola Hastings – disguised as her twin brother at boarding school. Joining forces with Channing Tatum in his breakout role, they engage in entertaining onscreen banter under Andy Fickman's direction. This rom-com delves into themes revolving around gender roles and identity while providing comedic moments and captivating performances from emerging talents like Alex Breckenridge.
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9
Mamma Mia!
Meryl Streep, Pierce Brosnan, Colin Firth
287 votes
Mamma Mia! brought ABBA's timeless music back into cultural relevancy with an all-star cast including Meryl Streep, Amanda Seyfried, Pierce Brosnan, Colin Firth, and Stellan Skarsgård. Directed by Phyllida Lloyd, it tells the story of Sophie Sheridan (Seyfried) attempting to discover her father’s identity before her wedding day amidst sun-soaked Mediterranean shores. Adapted from its successful Broadway namesake musical counterpart - this feel-good film earned critical acclaim featuring infectious songs deconstructing themes regarding parenthood revelation creating perfect escapism for audiences.
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10
50 First Dates
Adam Sandler, Drew Barrymore, Rob Schneider
512 votes
50 First Dates pairs Adam Sandler with Drew Barrymore in this unique romantic comedy set in Hawaii as they meet during unusual circumstances. Directed by Peter Segal, the film chronicles Sandler's character Henry Roth pursuing repetitive courtship due to Barrymore's Lucy Whitmore suffering from short-term memory loss. With a subtle exploration of disability and commitment at its core, 50 First Dates established itself as a heartfelt rom-com full of innovative storytelling devices punctuated by captivating scenic backdrops.
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11
The Princess Diaries 2: Royal Engagement
Anne Hathaway, Julie Andrews, Héctor Elizondo
266 votes
The Princess Diaries 2: Royal Engagement picks up where its predecessor concluded, continuing Mia’s (Anne Hathaway) journey into Genovian royalty under Queen Clarisse Renaldi's (Julie Andrews) careful watch. Directed by Garry Marshall once again, this coming-of-age comedy traces an arranged marriage executed for political reasons but is further complicated when Mona enters the picture alongside Nicholas Devereaux (Chris Pine). Supported by great ensemble cast performances and an unforgettable sleepover sing-along scene, it cemented The Princess Diaries' duo as beloved family movies with an epic romantic payoff.
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12
A Cinderella Story
Hilary Duff, Jennifer Coolidge, Chad Michael Murray
224 votes
A Cinderella Story reimagines the classic tale in a modern setting starring Hilary Duff and Chad Michael Murray. Mark Rosman’s direction revolves around high school romance blossoming amidst clever disguise centering themes of identity and destiny filled with witty dialogue perfect for young audiences craving updated fairy tales.
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13
Sweet Home Alabama
Reese Witherspoon, Josh Lucas, Patrick Dempsey
399 votes
Sweet Home Alabama sees Reese Witherspoon starring as Melanie Smooter/Carmichael – a young woman on the cusp of marital bliss only to discover her past nuptials remain valid. Directed by Andy Tennant, viewers are reunited with one not-so-loveable ex-husband named Jake Perry (Josh Lucas), whose rekindled connection provides the perfect dose of quintessential Southern charm making audiences question which side they're rooting for while examining true love versus superficial attraction. This charming mash-up triumphs because Witherspoon convincingly balances vulnerability against determination proving there’s always hope regardless of how deep our roots go.
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14
Enchanted
Amy Adams, Patrick Dempsey, James Marsden
229 votes
Enchanted is Disney's delightful blend of live-action and animation starring Amy Adams as Giselle – a naïve princess who falls victim to dastardly magic pushing her into reality's harsh world where she encounters NYC lawyer Robert Philip (Patrick Dempsey). Through David Lima's direction, viewers witness post-modern spin on fairy tales weaving together elements of romance, comedy, and musical genres. Fueled by stellar performances from the ensemble cast, including James Marsden and Susan Sarandon, Enchanted is a joyful experience that earned three Academy Award nominations for Best Original Song.
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15
Two Weeks Notice
Sandra Bullock, Hugh Grant, Alicia Witt
310 votes
Two Weeks Notice showcases Sandra Bullock and Hugh Grant's unbeatable chemistry as an ambitious attorney named Lucy Kelson and her charming yet needy boss George Wade – characters thrown into hilariously relatable scenarios involving professional collaboration turned tender affection. Marc Lawrence's directorial insight cleverly modernizes classic screwball comedy antics while providing an intriguing platform addressing issues concerning gentrification across urban landscapes, emphasizing love transcends personal convictions. It breaks down barriers and unites individuals despite stark societal contrasts.
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16
Love Actually
Hugh Grant, Laura Linney, Colin Firth
406 votes
Love Actually is a star-studded romantic comedy weaving together multiple love stories amidst the holiday season. Directed by renowned writer Richard Curtis, this beloved film stars countless talented actors, including Hugh Grant, Emma Thompson, Colin Firth, Keira Knightley, and Alan Rickman. Its exploration of different facets of love leaves us both heartbroken and hopeful as the intertwining narratives unfold while managing to touch upon serious topics like infidelity, grief, and unrequited love - all contributing to making Love Actually an enduring holiday classic.
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17
What a Girl Wants
Amanda Bynes, Colin Firth, Kelly Preston
143 votes
What a Girl Wants takes us on a journey with Amanda Bynes playing Daphne Reynolds, an American teenager reconnecting with her estranged British father. Directed by Dennie Gordon, this film merges comedy and emotion while underlining the concept of self-identity during adolescent years within familial relationships.
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18
Serendipity
John Cusack, Kate Beckinsale, Molly Shannon
258 votes
Serendipity is an enchanting John Cusack and Kate Beckinsale-led film that emphasizes the idea of "meant to be." Directed by Peter Chelsom, the movie follows the two leads as they toe the line between fate and free will after sharing a chance encounter in New York City. Stunning visuals from iconic locations summon millions toward its unique quality while threading a delicate depiction of love's grand design that challenges viewers' perception of destiny.
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19
Bridget Jones's Diary
Renée Zellweger, Colin Firth, Hugh Grant
368 votes
Bridget Jones’s Diary explores Renee Zellweger’s transformation into Helen Fielding’s beloved titular character facing life choices while being caught up between two prospective suitors: her dashing boss (played by Hugh Grant) and standoffish childhood friend (portrayed by Colin Firth). Sharon Maguire brilliantly recreates London on-screen with humor-spirited dialogue while traversing themes such as body image stigma fulfillment challenges faced amid late-stage singledom;The movie received accolades throughout Hollywood, proving itself a consummate 2000s-era rom-com.
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20
The Wedding Planner
Jennifer Lopez, Matthew McConaughey, Bridgette Wilson-Sampras
340 votes
The Wedding Planner stars Jennifer Lopez as Mary Fiore – an up-and-coming wedding planner who accidentally falls for her biggest client's fiancé Steve Edison (Matthew McConaughey), leading to unexpected chemistry and chaos. Directed by Adam Shankman, his romantic comedy excels in balancing heartache with hope as characters struggle through their feelings against professional obligations.
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21
Definitely, Maybe
Ryan Reynolds, Isla Fisher, Abigail Breslin
328 votes
Definitely, Maybe follows Ryan Reynolds' effortlessly charming portrayal of Will Hayes —a father explaining his complex past relationship history to his daughter— while connecting dots that lead them to her mother's identity. Overflowing with heartwarming anecdotes backed by Elizabeth Banks, Isla Fisher, and Rachel Weisz, who collectively portray Will's former loves, writer-director Adam Brooks skillfully crafts a layered cinematic experience that doubles as a nostalgic time capsule traversing early 90s politics through plots full of twists and turns.
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22
He's Just Not That Into You
Ben Affleck, Jennifer Aniston, Drew Barrymore
229 votes
He's Just Not That Into You is an ensemble rom-com starring Jennifer Aniston, Ben Affleck, Scarlett Johansson, and more. Directed by Ken Kwapis, this charming and honest take on modern relationships captures the complications and interconnections within the dating world, making it a relatable experience for viewers.
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23
The Wedding Date
Debra Messing, Dermot Mulroney, Amy Adams
282 votes
The Wedding Date features Debra Messing in a captivating performance as Kat Ellis – a woman who hires a male escort (Dermot Mulroney) to be her date for her sister's wedding. Directed by Clare Kilner with charming chemistry between leads resulting from great dialogue delivery showcasing their prowess in mastering various comedic scenarios throughout believable performances, it manages simultaneously remind viewers despite the seemingly cynical outlook culture regarding online dating evolution over time… nonetheless, there remains risk involved vulnerability required truly embrace connection genuine partnership experience reflecting lighthearted humor romance-based cinema enjoyment audiences everywhere.
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24
Maid in Manhattan
Jennifer Lopez, Ralph Fiennes, Natasha Richardson
188 votes
Maid in Manhattan showcases Jennifer Lopez as Marisa Ventura, a hotel maid mistaken for a socialite by a charming politician (Ralph Fiennes). Directed by Wayne Wang, the film perfectly blends themes of deception and love while highlighting the importance of staying true to oneself.
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25
Hitch
Will Smith, Eva Mendes, Kevin James
370 votes
Hitch showcases Will Smith as New York City's "Date Doctor," who seemingly has all answers until he meets gossip columnist Sara Melas (Eva Mendes). Under Andy Tennant’s direction, it provides a humorous insight into dating intricacies against the vibrant Manhattan backdrop.
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26
Confessions of a Shopaholic
Isla Fisher, Hugh Dancy, Krysten Ritter
229 votes
Confessions of a Shopaholic allows Isla Fisher to shine as Rebecca Bloomwood – a young woman drowning in debt yet seeking employment within the high-flying world of finance journalism under Luke Brandon’s tutelage (played by Hugh Dancy). P.J Hogan’s directing expertise creates a visually lush landscape peppered with hilariously chaotic moments, offering not only laughs but also an underlying commentary on consumerist cultural values.
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27
Wedding Crashers
Owen Wilson, Vince Vaughn, Christopher Walken
262 votes
Wedding Crashers features Owen Wilson and Vince Vaughn as two adventurous friends who crash weddings only to find real connections. Directed by David Dobkin, the film draws laughter with light-hearted humor threaded through romantic predicaments for its characters.
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28
Bride Wars
Kate Hudson, Anne Hathaway, Kristen Johnston
277 votes
Bride Wars tests the limits of friendship between Liv (Kate Hudson) and Emma (Anne Hathaway), whose weddings end up on the same day. Gary Winick directs this comedic take on bridal competition, unraveling deep-rooted emotions amidst outrageous fights and misunderstandings, earning an entertaining watch.
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29
Forgetting Sarah Marshall
Jason Segel, Kristen Bell, Mila Kunis
321 votes
Forgetting Sarah Marshall follows composer Peter Bretter (Jason Segel) struggling to get over his TV actress ex-girlfriend on a picturesque Hawaiian vacation. Directed by Nicholas Stoller, it provides relatable humor steeped in heartache and self-discovery set amid breath-taking locations making it a memorable addition to the rom-com genre.
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30
Made of Honor
Patrick Dempsey, Michelle Monaghan, Kevin McKidd
135 votes
Made of Honor stars Patrick Dempsey as Tom – a platonic friend who realizes his love for Hannah (Michelle Monaghan) when she asks him to be her "maid" of honor. Paul Weiland's rom-com showcases the importance of friendship in romantic relationships delivering an enjoyable journey navigating complicated emotional terrains.
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31
Monster-in-Law
Jennifer Lopez, Jane Fonda, Michael Vartan
218 votes
Monster-in-Law stars Jennifer Lopez and Jane Fonda in a fierce comedic battle as the bride-to-be and her disapproving future mother-in-law. Directed by Robert Luketic, the film offers uproarious moments with underlying messages about love, family, and acceptance despite differences.
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32
The 40-Year-Old Virgin
Steve Carell, Catherine Keener, Paul Rudd
227 votes
The 40-Year-Old Virgin features Steve Carell as Andy Stitzer, who undergoes hilarious attempts to lose his virginity. Helmed by Judd Apatow, this humorous masterpiece tackled sensitive topics entrusting viewers with sidesplitting episodes filled with unexpected romance.
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33
Along Came Polly
Ben Stiller, Jennifer Aniston, Philip Seymour Hoffman
178 votes
Along Came Polly presents Ben Stiller as risk-averse Reuben, who reconnects with free-spirited Polly (Jennifer Aniston) after his marriage collapses. Directed by John Hamburg, this romantic comedy illustrates the beauty of stepping out of one's comfort zone while uncovering new opportunities for self-discovery and love.
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34
The Prince and Me
Julia Stiles, Luke Mably, Ben Miller
106 votes
The Prince and Me revolves around Paige (Julia Stiles), a college student who unknowingly falls for foreign student Eddie, secretly a Danish prince. Directed by Martha Coolidge, this romantic comedy explores cultural differences, vulnerability, and the surprising nature of love.
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35
Kate & Leopold
Meg Ryan, Hugh Jackman, Liev Schreiber
161 votes
Kate & Leopold tells a charming tale traversing through time involving a 19th-century Duke (Hugh Jackman) ending up in modern Manhattan, where he encounters scientist Kate McKay (Meg Ryan). Under James Mangold's direction, this delightful rom-com explores unexpected romance blossoming amid contrasting backgrounds while discovering shared values.
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36
What Women Want
Mel Gibson, Helen Hunt, Marisa Tomei
203 votes
What Women Want features Mel Gibson as chauvinistic executive Nick Marshall, who gains the ability to hear women's thoughts and encounters advertising genius Darcy (Helen Hunt). Directed by Nancy Meyers, this charming rom-com displays themes of empathy and understanding while providing sharp humor infused with intelligent commentary on gender biases.
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37
Just My Luck
Lindsay Lohan, Chris Pine, Samaire Armstrong
98 votes
Just My Luck stars Lindsay Lohan as Ashley, a girl whose fortune is reversed when she encounters unlucky stranger Jake (Chris Pine). Directed by Donald Petrie, this amusing rom-com masterfully incorporates supernatural elements while exploring the concept of fate, destiny, and coincidences in finding love.
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38
Something's Gotta Give
Jack Nicholson, Diane Keaton, Keanu Reeves
171 votes
Something's Gotta Give focuses on playboy Harry Sanborn (Jack Nicholson), who reevaluates his lifestyle after falling for Erica Barry (Diane Keaton), the mother of his girlfriend. Nancy Meyers directs this charming rom-com that delves into relationship dynamics across age gaps with humor and sincerity.
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39
The Girl Next Door
Emile Hirsch, Elisha Cuthbert, Timothy Olyphant
84 votes
A comedy/drama film based on the novel of the same name, The Girl Next Door follows a suburbanite who falls for his new neighbor, only to discover she is a former adult film star looking to start a new life. Matthew Kidman's directorial debut explores themes of love, moral ambiguity, and preconceived notions about people from different walks of life.
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40
The Sweetest Thing
Cameron Diaz, Christina Applegate, Selma Blair
88 votes
The Sweetest Thing demonstrates Cameron Diaz's flair for comedy, playing Christina Walters navigating the dating world's unpredictability alongside best friends Courtney (Christina Applegate) and Jane (Selma Blair), directed by Roger Kumble. This light-hearted film represents modern romances layered with hilarious events sporting distinctively engaging chemistry between characters.
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41
The Perfect Man
Hilary Duff, Heather Locklear, Chris Noth
75 votes
The Perfect Man stars Hilary Duff as a teenager attempting to find a suitable partner for her single mother (Heather Locklear). This delightful film, directed by Mark Rosman, combines romance, family dynamics, and the quest for love, offering viewers an engaging story filled with warmth and laughter.
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42
The Break-Up
Vince Vaughn, Jennifer Aniston, Joey Lauren Adams
99 votes
The Break-Up features Jennifer Aniston and Vince Vaughn as a couple going through a tumultuous separation while sharing the same living space. Directed by Peyton Reed, this rom-com takes a unique approach to relationships, exploring the complexities and challenges of breakups with humor and heartache.
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43
Nick & Norah's Infinite Playlist
Kat Dennings, Michael Cera, Mimi Imfurst
115 votes
Nick & Norah's Infinite Playlist is an indie romantic comedy featuring Michael Cera and Kat Dennings as two music lovers who embark on a night-long adventure in search of a secret show. Under Peter Sollett's direction, the film captures the magic of young love set against the backdrop of New York City's vibrant music scene.
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- #13 of 20 onUnderrated Sleepover Movies Worth Staying Up All Night For
44
Just Friends
Ryan Reynolds, Amy Smart, Anna Faris
108 votes
Just Friends explores the intricacies of friendship-turned-romance starring Ryan Reynolds as Chris, a former high school nerd reconnecting with his one true crush Jamie (Amy Smart), years later in life. The movie, directed by Roger Kumble, provides hearty laughs and relatable themes surrounding vulnerability and timing within relationships.
More Just Friends
- #586 of 704 onThe All-Time Greatest Comedy Films
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45
Fever Pitch
Drew Barrymore, Jimmy Fallon, James B. Sikking
140 votes
Fever Pitch stars Drew Barrymore and Jimmy Fallon in a romantic comedy that revolves around a high school teacher's (Fallon) fanatical devotion to the Boston Red Sox, which complicates his blossoming relationship with a workaholic executive (Barrymore). Directed by the Farrelly brothers, the film delivers genuine laughs and heartfelt moments while examining the role of passion and compromise in relationships.
More Fever Pitch
- #113 of 209 onThe Best Sports Movies Ever Made
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46
It's Complicated
Meryl Streep, Steve Martin, Alec Baldwin
128 votes
In this romantic comedy, Meryl Streep stars as a divorced woman who finds herself in an unexpected love triangle after rekindling a sexual relationship with her ex-husband (Alec Baldwin), who is now remarried. Directed by Nancy Meyers, It's Complicated takes a humorous yet thoughtful look at the complexities of love and relationships later in life.
More It's Complicated
- #279 of 473 onThe 400+ Best Chick Flicks Ever
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47
Win a Date with Tad Hamilton!
Kate Bosworth, Topher Grace, Josh Duhamel
123 votes
A small-town girl wins a contest to go on a date with one of the world's biggest male celebrities in this romantic comedy. Win a Date With Tad Hamilton! stars Kate Bosworth as the smitten fan who must decide between her real-life friendship and her fantasy celebrity crush.
More Win a Date with Tad Hamilton!
- #352 of 473 onThe 400+ Best Chick Flicks Ever
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48
Rumor Has It
Jennifer Aniston, Kevin Costner, Shirley MacLaine
85 votes
Rumor Has It, directed by Rob Reiner, features Jennifer Aniston searching her past to uncover family secrets surrounding the potential inspiration for the novel "The Graduate." Incorporating romance with a generational plot, Kevin Costner and Mark Ruffalo bring depth to their roles, creating a unique blend of nostalgia and modern love.
49
Must Love Dogs
Diane Lane, John Cusack, Elizabeth Perkins
138 votes
Must Love Dogs features Diane Lane as a recently divorced preschool teacher thrust into the online dating world by her well-meaning sister. Directed by Gary David Goldberg, this charming rom-com explores the trials of modern dating, self-discovery, and the power of second chances in love, all while showcasing the undeniable chemistry between Lane and her love interest, portrayed by John Cusack.
More Must Love Dogs
- #293 of 473 onThe 400+ Best Chick Flicks Ever
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50
Someone Like You
Ashley Judd, Greg Kinnear, Hugh Jackman
111 votes
After getting dumped by her boyfriend, a talented twentysomething talk show talent scout (Ashley Judd) swears off relationships until she meets a few potential new suitors. Someone Like You explores themes of heartbreak, finding oneself, and the challenges of dating and relationships in your 20s and 30s.
More Someone Like You
- #60 of 113 onThe Best Movies Of 2001
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51
Shallow Hal
Gwyneth Paltrow, Jack Black, Jason Alexander
106 votes
Shallow Hal, directed by the Farrelly brothers, takes a comedic approach to appearances and self-image as Jack Black's character Hal starts seeing inner beauty after being hypnotized by a self-help guru. Gwyneth Paltrow co-stars as Rosemary, challenging preconceived notions of attractiveness in this quirky romantic comedy with an underlying message of acceptance and love.
More Shallow Hal
- #255 of 634 onThe 600+ Funniest Movies Of All Time
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52
Four Christmases
Vince Vaughn, Reese Witherspoon, Robert Duvall
76 votes
Four Christmases follows Reese Witherspoon and Vince Vaughn as a couple navigating numerous family gatherings during the holidays. Directed by Seth Gordon, the film highlights relatable dysfunctional relationship dynamics faced amidst festive chaos, proving there's heartwarming comedy gold within blended family bonding.
More Four Christmases
- #50 of 126 onThe Best Christmas Movies Of All Time
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53
Knocked Up
Seth Rogen, Katherine Heigl, Paul Rudd
200 votes
An up-and-coming career girl named Alison (Katherine Heigl) gets pregnant after a drunken one-night stand with slacker Ben (Seth Rogen), leading to an unlikely relationship as the two try to make their improbable situation work. Written and directed by Judd Apatow, Knocked Up is a raunchy yet heartfelt look at the complications of unplanned pregnancy and the differences between young adults at different life stages.
More Knocked Up
- #500 of 705 onThe All-Time Greatest Comedy Films
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54
Couples Retreat
Vince Vaughn, Jason Bateman, Jon Favreau
73 votes
Couples Retreat follows four pairs trying to salvage their relationships through group therapy sessions at an island resort, leading to comedic chaos. Directed by Peter Billingsley and starring Vince Vaughn and Kristen Bell, this film keeps viewers engaged throughout hysterical misadventures set against a picturesque backdrop.
More Couples Retreat
- #674 of 704 onThe All-Time Greatest Comedy Films
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55
Sex and the City
Sarah Jessica Parker, Kim Cattrall, Chris Noth
167 votes
Sex and the City is a rom-com drama that sweeps its audience into the bustling, glamorous life of Manhattan. Our protagonist, Carrie Bradshaw (Sarah Jessica Parker), navigates love and friendship with her three best friends - Samantha Jones (Kim Cattrall), Miranda Hobbes (Cynthia Nixon), and Charlotte York (Kristin Davis). Set against a backdrop of high fashion and higher stakes, the movie explores their romantic escapades and personal dilemmas. The film, an extension of the award-winning TV series, cleverly intertwines humor, heartbreak, and hope while showcasing the complexities of modern womanhood.
More Sex and the City
- #109 of 473 onThe 400+ Best Chick Flicks Ever
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56
Bewitched
Nicole Kidman, Will Ferrell, Shirley MacLaine
60 votes
Based on the classic 1960s sitcom, Bewitched stars Nicole Kidman as a real-life witch who is cast in a remake of the show, while Will Ferrell plays the insecure actor hired to be her on-screen husband. This romantic fantasy comedy puts a meta spin on the original premise, exploring the behind-the-scenes challenges of reviving an iconic series.
More Bewitched
- #142 of 143 onThe Best Movies of 2005
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57
Imagine Me & You
Piper Perabo, Lena Headey, Matthew Goode
46 votes
During her wedding ceremony, Rachel (Piper Perabo) notices Luce (Lena Headey) in the audience and feels instantly drawn to her. The two women become close friends, and when Rachel learns that Luce is a lesbian, she realizes that despite her happy marriage to Heck (Matthew Goode), she is falling for Luce. As she questions her sexual orientation, Rachel must decide between her stable relationship with Heck and her exhilarating new romance with Luce.
More Imagine Me & You
- #4 of 32 onGreat Mainstream Movies About Lesbians
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58
Little Black Book
Brittany Murphy, Holly Hunter, Kathy Bates
51 votes
Stacey (Brittany Murphy) is an associate producer for a daytime talk show featuring Kippie Kann (Kathy Bates). She's upset that her boyfriend, Derek (Ron Livingston), won't talk about his past relationships. With encouragement from her co-worker Barb (Holly Hunter), Stacey steals Derek's phone, contacts his ex-girlfriends and interviews them under the pretense that they'll be on the show. But things get complicated when Stacey forms a friendship with one of the girls (Julianne Nicholson).
59
Laws of Attraction
Pierce Brosnan, Julianne Moore, Michael Sheen
81 votes
Audrey Woods (Julianne Moore) and Daniel Rafferty (Pierce Brosnan) are rival divorce lawyers who are complete opposites: She relies on the law, while he relies on personality. They are hired to represent opposing sides of a celebrity divorce case involving a rock star (Michael Sheen), a dress designer (Parker Posey) and a custody dispute over an Irish castle. Audrey and Daniel wind up in Ireland together, where, to their astonishment, sparks fly between them.
60
Guess Who
Bernie Mac, Ashton Kutcher, Zoe Saldana
48 votes
Theresa (Zoe Saldana) is a young woman who is about to introduce her fiancé to her father, Percy Jones (Bernie Mac). Percy is eager to meet his African-American daughter's businessman beau, but is shocked to learn that she is engaged to Simon Green (Ashton Kutcher), a white man. Staying with the Joneses to celebrate Percy and his wife's 25th wedding anniversary, the accident-prone Simon makes a terrible first impression and faces an uphill battle to win over his future father-in-law.
More Guess Who
- #95 of 143 onThe Best Movies of 2005
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Win a Date with Tad Hamilton!