The Best Romantic Comedies Of The 2000s, Ranked By Fans
- Kate Hudson, Matthew McConaughey, Adam Goldberg
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.
- #612 of 705 onThe All-Time Greatest Comedy Films
- #396 of 769 onThe Most Rewatchable Movies
- #9 of 136 onThe 100+ Best Movies For Date Night
- Sandra Bullock, Ryan Reynolds, Mary Steenburgen
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.
More The Proposal- #259 of 634 onThe 600+ Funniest Movies Of All Time
- #6 of 136 onThe 100+ Best Movies For Date Night
- #6 of 473 onThe 400+ Best Chick Flicks Ever
- Reese Witherspoon, Luke Wilson, Selma Blair
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.
More Legally Blonde- #188 of 769 onThe Most Rewatchable Movies
- #112 of 705 onThe All-Time Greatest Comedy Films
- #42 of 66 onMovies You Wish You Could Still Watch for the First Time
- Julie Andrews, Anne Hathaway, Héctor Elizondo
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.
More The Princess Diaries- #319 of 769 onThe Most Rewatchable Movies
- #68 of 375 onThe Best Movies Based On Books
- #18 of 113 onThe Best Movies Of 2001
- Jennifer Garner, Mark Ruffalo, Judy Greer
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.
More 13 Going on 30- #424 of 769 onThe Most Rewatchable Movies
- #43 of 155 onThe 150+ Best Classic Tween Movies
- #25 of 99 onThe Best Movies Of 2004, Ranked
- Sandra Bullock, Michael Caine, Benjamin Bratt
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.
More Miss Congeniality- #104 of 705 onThe All-Time Greatest Comedy Films
- #125 of 769 onThe Most Rewatchable Movies
- #74 of 634 onThe 600+ Funniest Movies Of All Time
- Katherine Heigl, James Marsden, Malin Akerman
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.
More 27 Dresses- #18 of 473 onThe 400+ Best Chick Flicks Ever
- #36 of 82 onThe Greatest Female-Led Comedy Movies
- #128 of 185 onMovies With The Best Soundtracks
- Amanda Bynes, James Kirk, Channing Tatum
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.
More She's the Man- #21 of 46 on50+ Quirky Romance Movies With Unique Love Stories
- #76 of 101 onThe Best Movies Of 2006
- #15 of 473 onThe 400+ Best Chick Flicks Ever
- Meryl Streep, Pierce Brosnan, Colin Firth
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.
More Mamma Mia!- #592 of 769 onThe Most Rewatchable Movies
- #9 of 204 onMusical Movies With The Best Songs
- #16 of 31 onThe Most Gorgeous Movie Wedding Dresses, Ranked
- Adam Sandler, Drew Barrymore, Rob Schneider
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.
More 50 First Dates- Dig Deeper...50 First Dates Isn't Romantic - It's About A Guy Who Takes Advantage Of A Disabled Woman
- #113 of 769 onThe Most Rewatchable Movies
- #252 of 705 onThe All-Time Greatest Comedy Films
- Anne Hathaway, Julie Andrews, Héctor Elizondo
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.
- #61 of 99 onThe Best Movies Of 2004, Ranked
- #43 of 82 onThe 75+ Best Fairytale Movies
- #13 of 170 onThe 150+ Best Teen Romance Movies, Ranked
- Hilary Duff, Jennifer Coolidge, Chad Michael Murray
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.
More A Cinderella Story- #69 of 136 onThe 100+ Best Movies For Date Night
- #62 of 82 onThe 75+ Best Fairytale Movies
- #9 of 170 onThe 150+ Best Teen Romance Movies, Ranked
- Reese Witherspoon, Josh Lucas, Patrick Dempsey
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.
More Sweet Home Alabama- #265 of 769 onThe Most Rewatchable Movies
- #10 of 136 onThe 100+ Best Movies For Date Night
- #45 of 152 onThe Best Movies of 2002
- Amy Adams, Patrick Dempsey, James Marsden
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.
More Enchanted- #453 of 769 onThe Most Rewatchable Movies
- #46 of 204 onMusical Movies With The Best Songs
- #99 of 453 onThe 400+ Best Animated Kids Movies
- Sandra Bullock, Hugh Grant, Alicia Witt
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.
More Two Weeks Notice- #97 of 152 onThe Best Movies of 2002
- #80 of 473 onThe 400+ Best Chick Flicks Ever
- #44 of 243 onThe Best Movies For Women
- Hugh Grant, Laura Linney, Colin Firth
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.
More Love Actually- Dig Deeper...14 Disturbing and Heinously Sexist Things You Never Noticed About 'Love, Actually'
- #462 of 769 onThe Most Rewatchable Movies
- #34 of 126 onThe Best Christmas Movies Of All Time
- Amanda Bynes, Colin Firth, Kelly Preston
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.
More What a Girl Wants- #48 of 170 onThe 150+ Best Teen Romance Movies, Ranked
- #52 of 473 onThe 400+ Best Chick Flicks Ever
- #39 of 82 onThe Greatest Female-Led Comedy Movies
- John Cusack, Kate Beckinsale, Molly Shannon
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.
More Serendipity- #89 of 126 onThe Best Christmas Movies Of All Time
- #52 of 113 onThe Best Movies Of 2001
- #36 of 136 onThe 100+ Best Movies For Date Night
- Renée Zellweger, Colin Firth, Hugh Grant
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.
- #658 of 769 onThe Most Rewatchable Movies
- #48 of 136 onThe 100+ Best Movies For Date Night
- #37 of 113 onThe Best Movies Of 2001
- Jennifer Lopez, Matthew McConaughey, Bridgette Wilson-Sampras
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.
More The Wedding Planner- #62 of 113 onThe Best Movies Of 2001
- #60 of 136 onThe 100+ Best Movies For Date Night
- #45 of 473 onThe 400+ Best Chick Flicks Ever
- Ryan Reynolds, Isla Fisher, Abigail Breslin
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.
More Definitely, Maybe- #85 of 473 onThe 400+ Best Chick Flicks Ever
- #15 of 57 onThe Best Single Dad Movies Ever Made
- #33 of 87 onThe 80+ Best Father-Daughter Movies
- Ben Affleck, Jennifer Aniston, Drew Barrymore
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.
- #104 of 473 onThe 400+ Best Chick Flicks Ever
- #14 of 60 onRomantic Movies Your Girlfriend Forces You To Watch
- #224 of 243 onThe Best Movies For Women
- Debra Messing, Dermot Mulroney, Amy Adams
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.
More The Wedding Date- #103 of 143 onThe Best Movies of 2005
- #110 of 473 onThe 400+ Best Chick Flicks Ever
- #8 of 25 onIf Your Partner Suggests Any Of These Movies, They Want An Engagement Ring
- Jennifer Lopez, Ralph Fiennes, Natasha Richardson
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.
More Maid in Manhattan- #80 of 136 onThe 100+ Best Movies For Date Night
- #87 of 152 onThe Best Movies of 2002
- #64 of 473 onThe 400+ Best Chick Flicks Ever
- Will Smith, Eva Mendes, Kevin James
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.
More Hitch- #605 of 704 onThe All-Time Greatest Comedy Films
- #71 of 136 onThe 100+ Best Movies For Date Night
- #41 of 143 onThe Best Movies of 2005
- Isla Fisher, Hugh Dancy, Krysten Ritter
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.
- #314 of 375 onThe Best Movies Based On Books
- #76 of 473 onThe 400+ Best Chick Flicks Ever
- #157 of 185 onMovies With The Best Soundtracks
- Owen Wilson, Vince Vaughn, Christopher Walken
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.
More Wedding Crashers- #335 of 769 onThe Most Rewatchable Movies
- #66 of 705 onThe All-Time Greatest Comedy Films
- #73 of 136 onThe 100+ Best Movies For Date Night
- Kate Hudson, Anne Hathaway, Kristen Johnston
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.
More Bride Wars- #78 of 89 onThe Most Rewatchable Comedy Movies
- #66 of 473 onThe 400+ Best Chick Flicks Ever
- #46 of 82 onThe Greatest Female-Led Comedy Movies
- Jason Segel, Kristen Bell, Mila Kunis
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.
- #624 of 769 onThe Most Rewatchable Movies
- #373 of 705 onThe All-Time Greatest Comedy Films
- #59 of 136 onThe 100+ Best Movies For Date Night
- Patrick Dempsey, Michelle Monaghan, Kevin McKidd
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.
More Made of Honor - Jennifer Lopez, Jane Fonda, Michael Vartan
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.
More Monster-in-Law- #257 of 473 onThe 400+ Best Chick Flicks Ever
- #9 of 31 onThe Most Gorgeous Movie Wedding Dresses, Ranked
- #25 of 64 onThe 60+ Best Movies About Weddings
- Steve Carell, Catherine Keener, Paul Rudd
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.
- #503 of 769 onThe Most Rewatchable Movies
- #49 of 705 onThe All-Time Greatest Comedy Films
- #39 of 634 onThe 600+ Funniest Movies Of All Time
- Ben Stiller, Jennifer Aniston, Philip Seymour Hoffman
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.
More Along Came Polly- #85 of 99 onThe Best Movies Of 2004, Ranked
- #416 of 473 onThe 400+ Best Chick Flicks Ever
- #27 of 70 onThe Best Movies About Getting Dumped
- Julia Stiles, Luke Mably, Ben Miller
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.
More The Prince and Me- #80 of 99 onThe Best Movies Of 2004, Ranked
- #92 of 473 onThe 400+ Best Chick Flicks Ever
- #49 of 170 onThe 150+ Best Teen Romance Movies, Ranked
- Meg Ryan, Hugh Jackman, Liev Schreiber
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.
More Kate & Leopold- #543 of 769 onThe Most Rewatchable Movies
- #94 of 113 onThe Best Movies Of 2001
- #193 of 473 onThe 400+ Best Chick Flicks Ever
- Mel Gibson, Helen Hunt, Marisa Tomei
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.
More What Women Want- #116 of 473 onThe 400+ Best Chick Flicks Ever
- #44 of 56 onThe Funniest Movies Starring SNL Cast Members
- #26 of 32 onBlockbusters With No Cultural Impact Whatsoever, Ranked
- Lindsay Lohan, Chris Pine, Samaire Armstrong
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.
More Just My Luck- #198 of 243 onThe Best Movies For Women
- #16 of 20 onUnderrated Sleepover Movies Worth Staying Up All Night For
- #6 of 71 on70+ Movies And Shows With Luck In The Title
- Jack Nicholson, Diane Keaton, Keanu Reeves
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.
- #174 of 473 onThe 400+ Best Chick Flicks Ever
- #46 of 60 onRomantic Movies Your Girlfriend Forces You To Watch
- #1 of 55 onThe Best Movies About Falling in Love Late in Life, Ranked
- Emile Hirsch, Elisha Cuthbert, Timothy Olyphant
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.
More The Girl Next Door- #689 of 705 onThe All-Time Greatest Comedy Films
- #53 of 99 onThe Best Movies Of 2004, Ranked
- #225 of 473 onThe 400+ Best Chick Flicks Ever
- Cameron Diaz, Christina Applegate, Selma Blair
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.
More The Sweetest Thing- #76 of 152 onThe Best Movies of 2002
- #168 of 473 onThe 400+ Best Chick Flicks Ever
- #26 of 82 onThe Greatest Female-Led Comedy Movies
- Hilary Duff, Heather Locklear, Chris Noth
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.
More The Perfect Man- #105 of 170 onThe 150+ Best Teen Romance Movies, Ranked
- #355 of 473 onThe 400+ Best Chick Flicks Ever
- #54 of 62 onThe Best Romantic Comedies Rated PG
- Vince Vaughn, Jennifer Aniston, Joey Lauren Adams
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.
More The Break-Up- #698 of 705 onThe All-Time Greatest Comedy Films
- #84 of 101 onThe Best Movies Of 2006
- #301 of 473 onThe 400+ Best Chick Flicks Ever
- Kat Dennings, Michael Cera, Mimi Imfurst
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.
- Ryan Reynolds, Amy Smart, Anna Faris
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
- #89 of 136 onThe 100+ Best Movies For Date Night
- #25 of 70 onThe Funniest Christmas Comedy Movies
- Drew Barrymore, Jimmy Fallon, James B. Sikking
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
- #53 of 143 onThe Best Movies of 2005
- #25 of 93 onThe All-Time Best Baseball Films
- Meryl Streep, Steve Martin, Alec Baldwin
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
- #2 of 55 onThe Best Movies About Falling in Love Late in Life, Ranked
- #49 of 243 onThe Best Movies For Women
- 47
Win a Date with Tad Hamilton!
Kate Bosworth, Topher Grace, Josh DuhamelA 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.
- #352 of 473 onThe 400+ Best Chick Flicks Ever
- #45 of 62 onThe Best Movies with Rich People Spending Big
- #22 of 67 onGreat Movies About Male-Female Friendships
- Jennifer Aniston, Kevin Costner, Shirley MacLaine
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.
- Diane Lane, John Cusack, Elizabeth Perkins
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
- #11 of 27 onThe Best Movies About a Midlife Crisis in Women
- #123 of 322 onThe 200+ Best Romantic Comedies Of All Time
- Ashley Judd, Greg Kinnear, Hugh Jackman
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
- #359 of 473 onThe 400+ Best Chick Flicks Ever
- #22 of 25 onToast The New Year With The Top New Year's Eve Movie Scenes
- Gwyneth Paltrow, Jack Black, Jason Alexander
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
- #39 of 113 onThe Best Movies Of 2001
- #57 of 89 onThe Most Rewatchable Comedy Movies
- Vince Vaughn, Reese Witherspoon, Robert Duvall
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
- #12 of 70 onThe Funniest Christmas Comedy Movies
- #34 of 85 onThe Best Christmas Rom-Coms
- Seth Rogen, Katherine Heigl, Paul Rudd
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
- #231 of 634 onThe 600+ Funniest Movies Of All Time
- #29 of 93 onThe 85+ Best Stoner Comedies Ever
- Vince Vaughn, Jason Bateman, Jon Favreau
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
- #15 of 65 onThe Funniest Movies About Marriage
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- Sarah Jessica Parker, Kim Cattrall, Chris NothSex 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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- Nicole Kidman, Will Ferrell, Shirley MacLaine
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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- #421 of 473 onThe 400+ Best Chick Flicks Ever
- Piper Perabo, Lena Headey, Matthew GoodeDuring 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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- Brittany Murphy, Holly Hunter, Kathy BatesStacey (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).
- Pierce Brosnan, Julianne Moore, Michael SheenAudrey 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.
- Bernie Mac, Ashton Kutcher, Zoe SaldanaTheresa (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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