60 Best Romantic Comedies For Movie Night

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In the mood for a movie with a killer romance wrapped in a lovely comedic package? These rom-coms will make you swoon, laugh and fall in love with love. From 80s classics like Overboard and When Harry Met Sally to iconic teen flicks like 10 Things I Hate About You and 13 Going on 30, there’s a nice array of films perfect for your next movie marathon this weekend (or weekday, whatever rocks your socks)!

Never Been Kissed (1999)

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Going undercover as a student at her former high school should be easy for the fresh-faced Josie Geller (Drew Barrymore), but things quickly spin out of control when she falls for English teacher Sam Coulson (Michael Vartan).

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She’s All That (1999)

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She’s All That (1999) is a classic teen romantic comedy that is sure to make you laugh out loud. Following the downfall of Zach Siler’s (Freddie Prinze Jr.) reputation, he crafts a plan to transform the nerdy loner Laney Boggs (Rachael Leigh Cook) into the next prom queen. A light and predictable watch that doesn’t require much attention. 

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He’s Just Not That Into You (2009)

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He’s Just Not That into You features an all-star cast with many notable favorites: Ben, Affleck, Jennifer Aniston, Drew Barrymore, Jennifer Connelly, Kevin Connolly, Bradley Cooper, Ginnifer Goodwin, Scarlett Johansson and Justin Long. Following the love lives of a group of friends, this funny chick flick explores the complexities of contemporary relationships in all their confusing glory.

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Sixteen Candles (1984)

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Directed by John Hughes, Sixteen Candles offers all the 80’s nostalgia in this classic film starring Molly Ringwald who plays an angst-ridden Samantha, experiencing the worst sixteenth birthday when her entire family forgets. Add in her longtime crush Jake Ryan (Michael Schoeffling) and you have yourself an entertaining movie with an A-list cast. Still, that doesn’t take away from the problematic and disturbing issues apparent within the film. 

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She’s the Man (2006)

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Banned from joining the boys’ soccer team, Viola (Amanda Bynes) poses as her twin brother Sebastian at his new boarding school so she can play soccer. Things become complicated when she falls for her roommate Duke (Channing Tatum), especially when her brother returns sooner than expected only to find his sister pretending to be him.

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Enchanted (2007)

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Giselle’s (Amy Adams) plans to marry Prince Edward (James Marsden) are thwarted after his evil stepmother (Susan Sarandon) sends the future princess to New York City, a cold and harsh place compared to the fairytale land of Andalasia. Pessimistic divorce lawyer Robert (Robert Dempsey) comes to Giselle’s rescue and offers her a place to stay. As the days pass, the two become closer, but will true love conquer all? After all, love only exists in fairy tales, right?

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The Princess Diaries (2001)

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Anne Hathaway stars as Mia Thermopolis, an introverted teenager whose entire world is tipped off its axis when she learns she is the heir to the throne in the small country of Genovia. The road to becoming a princess is not easy however, especially when her no-nonsense grandmother, Queen Clarisse Renaldi (Julie Andrews), shows up to teach Mia how to be a princess.

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Legally Blonde (2001)

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Legally Blonde stars Reese Witherspoon as Elle Woods, a blonde sorority girl who challenges all stereotypes when she is admitted into Harvard Law School to win back her ex-boyfriend Warner (Matthew Davis). When Elle realizes how Warner views her, she is determined to prove everyone wrong by succeeding and she does so with determination, integrity and style.

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Mamma Mia! (2008)

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Based on the popular Broadway musical, this movie brings forth Amanda Seyfried as 20-year-old Sophie whose wedding day is quickly approaching. Hoping to figure out who her father is, Sophie invites three men from her mother Donna’s (Meryl Streep) past: Sam (Pierce Brosnan), Bill (Stellan Skarsgård) and Harry (Colin Firth). Sophie is set on having one of them walk her down the aisle on her big day, no matter the consequences. 

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Beyond the Lights (2014)

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With all eyes on her, superstar Noni Jean (Gugu Mbatha-Raw) feels she may crumble under the constant scrutiny and pressure that comes with being a world-famous singer. When the young cop Kaz (Nate Parker) enters her life on the night that she hits rock bottom, she is given a second chance at life and finding her voice.

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Someone Great (2019)

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When Jenny’s (Gina Rodriguez) longtime boyfriend Nate (Lakeith Stanfield) ends things, she’s heartbroken, lost and unsure of her future. But she’s not alone and with help from her two besties, Blair (Brittany Snow) and Erin (DeWanda Wise), Jenny manages to heal as they go on one last wild adventure in NYC before she moves to San Francisco for a new job as a music journalist.

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Emma (2020)

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Based on Jane Austen’s 1815 novel, Emma revolves around 21-year-old Emma Woodhouse (Anya Taylor-Joy), a young woman who can’t help but meddle in the lives of her loved ones by playing matchmaker. 

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Love, Simon (2018)

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An honest and heartfelt take on a young and closeted gay teen’s difficult journey to coming out. When 17-year-old Simon Spier (Nick Robinson) falls for an anonymous classmate online, he hopes to figure out who the mystery guy is which proves to be hilarious, tender, and, ultimately, life-changing.

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Say Anything (1989)

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Say Anything offers a charming and touching portrayal of first love. Lloyd (John Cusack), a high school senior, has his sights set on honor student, Diane Court (Ione Skye) who shares the sentiment, much to his surprise. 

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About Time (2013)

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When Tim Lake (Domhnall Gleeson) learns that he comes from a long line of time-traveling men, he decides it’s time to upgrade his life by getting a girlfriend. Enter Mary (Rachel McAdams).

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Always Be My Maybe (2019)

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Sasha Tran (Ali Wong) and Marcus Kim (Randall Park) are given a second chance at love in this heart-warming flick about two childhood sweethearts who had a falling out only to meet again 15 years later.  

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Overboard (1987)

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Goldie Hawn plays a hoity-toity heiress who suffers from a bad case of amnesia after falling from her yacht. Joanna’s husband Grant (Edward Herrmann) takes the chance to ditch his demanding wife. Meanwhile the widowed carpenter Dean (Kurt Russel), who was left unpaid after doing some work on her yacht, takes the chance to get his reimbursement.

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Hitch (2005)

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Will Smith and Eva Mendes star in this fun rom-com about Alex “Hitch” Hitchens, a guy who essentially teaches guys how to woo a girl, and Sara Melas, a gossip columnist. When Hitch falls for Sara, he is thrown through a loop after each of his tried and tested techniques fail to work.

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Crazy, Stupid, Love (2011)

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When Cal Weaver (Steve Carell) learns of his wife’s (Julianne Moore) infidelity and future plans of divorce, his perfect life takes a nosedive and puts him on a tailspin that involves getting advice from player extraordinaire Jacob Palmer (Ryan Gosling) who teaches Cal how to successfully navigate the dating world whilst Jacob finds himself slowly falls for recent law school graduate Hannah (Emma Stone).

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50 First Dates (2004)

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This 2004 funny chick flick features Adam Sandler as Henry Roth, a man set on wooing Lucy (Drew Barrymore) who suffers from a type of short-term memory loss where she forgets everything that happened the day before. Because of her memory loss, Henry is forced to win Lucy over every single day which creates an interesting and entertaining storyline for viewers.

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Knocked Up (2012)

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Knocked Up includes A-Listers Seth Rogen, Katherine Heigl, Leslie Mann and Paul Rudd. As the life of the party, babies were never a part of Ben Stone’s plan. After a one-night stand, those plans quickly fly out the window when he learns of Alison’s pregnancy.

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My Big Fat Greek Wedding (2002)

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Still unmarried at 30, Toula Portokalos’s (Nia Vardalos) entire family worries about her single lifestyle. When sparks fly between Toula and Ian Miller (John Corbett), a teacher who is most definitely not greek, she worries that her family will not approve of their impending marriage. If you’re looking for a feel-good romantic comedy that will make you laugh, add My Big Fat Greek Wedding to your movie marathon queue. 

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Love Jones (1997)

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After a chance encounter at a Chicago club, budding writer Darius Lovehall (Larenz Tate) and aspiring photographer Nina Mosley (Nia Long) are thrust into a whirlwind romance that is soon tested when she moves to New York to rekindle her relationship with her ex-fiancé.

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Moonstruck (1987)

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When Italian-American widowed bookkeeper Loretta (Cher) says “yes” to Johnny’s (Danny Aiello) marriage proposal, an ironic twist of fate sends her falling in love with his younger brother Ronny (Nicolas Cage). 

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The Holiday (2006)

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In the mood for a feel-good rom-com that’ll give you holiday vibes? The Holiday brings us a story of two women, Amanda Woods (Cameron Diaz) and Iris (Kate Winslet), who trade places and unexpectedly find love. 

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Silver Linings Playbook (2012)

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Jennifer Lawrence, Bradley Cooper and Robert De Niro star in this refreshing romantic comedy about a man, Pat Solitano, who returns home after being released from a psychiatric institution. While home, he meets the widow of a late friend, Tiffany, who offers to help him patch up his marriage if he does something very important for her in return.

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The Princess Bride (1987)

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Looking for a romantic comedy wrapped up in sword fights, giants, monsters, fencing and the adventure of a lifetime? The Princess Bride centers around a young princess on a mission to find her one true love. The catch? She thinks he’s dead.

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Definitely, Maybe (2008)

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When Maya Hayes (Abigail Breslin) asks her father Will (Ryan Reynolds) to tell the story of his life pre-marriage and how he fell in love with her mother, Will recounts his three relationships and changes the names of the women so that Maya can guess which one is her mom.  

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Groundhog Day (1993)

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Imagine reliving the worst day of your life over and over and over. A pessimistic weatherman (Bill Murray) finds himself in that exact situation, seemingly destined to relive February 2nd over and over and over again.

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Brown Sugar (2002)

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Hip-hop journalist Sidney (Sanaa Lathan) and record executive Andre (Taye Diggs) bonded over their love of music and can attribute their friendship and future careers to a single, defining moment from their past: observing the beginning of hip-hop on a street corner in New York. Now they’ll have to return to that day in order to fulfill their dreams.

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27 Dresses (2008)

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Wedding after wedding after wedding… Jane (Katherine Heigl) is a serial bridesmaid, making her the ultimate wedding guru. When her sister Tess (Malin Akerman) lands Jane’s long-time crush George (Edward Burns), she finds herself questioning everything as her world seemingly implodes, especially with the cute reporter Kevin (James Marsden) who is determined to get the dirt on Jane’s unique journey; always the bridesmaid and never the bride.

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Serendipity (2001)

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Jonathan Trager (John Cusack) and Sara Thomas (Kate Beckinsale) met while shopping for gloves at Bloomingdales. Both in committed relationships at the time, they decide to let fate determine their destiny.  

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There’s Something About Mary (1998)

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This wacky romantic date night flick is perfect for anyone who’s looking for a good laugh. Everyone wants to win over Mary Jensen (Cameron Diaz) which results in some hilarious situations.

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The Photograph (2020)

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In the wake of her mother’s death, Mae Morton (Issa Rae) discovers a photograph that sends her on a journey into her estranged mother’s past. While investigating, an unexpected affair blossoms between her and Michael Block (Lakeith Stanfield), an up-and-coming journalist.

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Breakfast at Tiffany’s (1961)

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This iconic classic tells the story of Holly Golightly (Audrey Hepburn), a young woman set on scoring an older rich man leading her to work as an escort and her upstairs neighbor, a New York writer dating an older wealthy woman. 

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Four Weddings and a Funeral (1994)

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When Charles (Hugh Grant) meets an American named Carrie (Andie MacDowell) at a wedding, they spend an unforgettable night together that is quickly cut short when she returns to the States. Over the course of their next four encounters, he becomes sure that they are destined for each other. 

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Something’s Gotta Give (2003)

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Diane Keaton and Jack Nicholson co-star in this rom-com about an older Casanova who goes with his younger girlfriend to her family’s beach house. Their romantic getaway is soon disrupted when mother, Erica Barry, chooses to stay for the weekend. When Harry suffers from a heart attack, he is advised to stay home and rest. In the process, he grows closer to Erica and soon realizes that she just may be the one woman that’s out of his league.

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The Wedding Singer (1998)

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After being left at the altar, wedding singer Robbie Hart loses all faith in love until the day Julia Sullivan (Drew Barrymore) walks into his life. His hope in love is slowly restored, but there’s one problem: she’s getting married. 

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Clueless (1995)

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Clueless is a must-watch romantic comedy for anyone who’s in the mood for a feel-good flick featuring memorable characters and plenty of quotable moments. This 1995 film centers around the shallow and rich teen Cher (Alicia Silverstone) who is at the top of the food chain at her Beverly Hills high school. After giving the helplessly klutzy new student Tai (Brittany Murphy) a makeover, she climbs the social ladder and becomes Queen B which leads Cher to realize that her ex-step-brother Josh (Paul Rudd) was right about her shallow outlook on life and you know what happens next (*wink wink*). “Ugh, as if.”

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The Big Sick (2017)

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The Big Sick revolves around Pakistani comic Kumail (Kumail Nanjiani) and American graduate student Emily (Zoe Kazan). After a chance encounter at one of his stand-up gigs, love blossoms between the two until disaster strikes, leaving Emily in a coma.

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Sweet Home Alabama (2002)

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When high-end fashion designer Melanie (Reese Witherspoon) becomes engaged to one of NYC’s most eligible bachelors, she finds herself in hot water. After all, on paper, she’s still married to her high school sweetheart Jake (Josh Lucas).

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Love & Basketball (2000)

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Childhood best friends Monica (Sanaa Lathan) and Quincy (Omar Epps) have always aspired to become professional basketball players. They never expected to fall in love. 

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The Wedding Planner (2001)

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Jennifer Lopez and Matthew McConaughey co-star in this cute rom-com about a wedding planner who breaks the cardinal rule: don’t fall for the groom. 

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The Proposal (2009)

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Big-time book editor Margaret Tate (Sandra Bullock) is faced with deportation to Canada. In an attempt to evade the law, Margaret devises a plan that involves marrying her assistant Andrew Paxton (Ryan Reynolds). 

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(500) Days of Summer (2009)

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When the love of his life dumps him, Tom (Joseph Gordon-Levitt) mulls over their time together to piece together where they went wrong. 

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Love Actually (2003)

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A Christmas romance flick that follows nine different stories, all intertwined in one way or another.

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How To Lose a Guy in 10 Days (2003)

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Feeling burnt out by her job as an advice columnist, Andie Anderson (Kate Hudson) decides to shake things up by writing a piece on how to lose a guy in 10 days. Andie quickly sets her sights on Ben Berry (Matthew McConaughey) who believes he can make any woman fall in love with him in the matter of 10 days. When these two clash, their resulting antics are hilarious in their absurdity. 

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Forgetting Sarah Marshall (2008)

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In an attempt to move on from his ex-girlfriend Sarah Marshall (Kristen Bell), struggling musician Peter Bretter (Jason Segel) goes on a trip to Hawaii, only to bump into Sarah while there.

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To All The Boys I’ve Loved Before (2018)

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After Lara Jean’s (Lana Condor) love letters are sent out to each of her past crushes, all hell breaks loose. Enter Peter Kavinsky (Noah Centineo).

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Bridget Jones’s Diary (2001)

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Renée Zellweger, Colin Firth and Hugh Grant star in this cute British rom-com about Bridget Jones, a 32-year-old woman who’s ready to hop in the driver’s seat and take control of her life. 

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Sleepless in Seattle (1993)

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In the wake of his wife’s passing, Sam Baldwin (Tom Hanks) moves to Seattle with his son Jonah (Ross Mallinger). One night, Jonah calls into a talk-radio show and persuades Sam to talk about his feelings on air. Reporter from Baltimore Annie Reed (Meg Ryan) falls for Sam after hearing him speak. The only problem, she’s engaged. 

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Think Like A Man (2012)

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When the guys learn their significant others are taking relationship pointers from Steve Harvey, they hatch a plot to turn the tides by reading the book and applying his lessons to their relationships as well. 

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My Best Friend’s Wedding (1997)

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Julia Roberts is the reigning queen of rom-coms and the 90s birthed some of her most prolific rom-coms yet. My Best Friend’s Wedding is one of those flicks, telling the story of a food critic who realizes she’s in love with her best friend after learning that he’s engaged to be married.  

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Pretty Woman (1990)

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When Vivian (Julia Roberts) hops into a Lotus, she never expects to be hired to play the part of girlfriend for an entire weekend. As the hours tick by, Vivian and Edward grow closer and closer, but their social backgrounds prove to be a difficult hurdle to overcome. 

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You’ve Got Mail (1998)

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Tom Hanks and Meg Ryan reunite in this charming flick about two enemies: a struggling small-business owner of a quant bookstore and the big-time owner of Foxbrooks, the chainstore across the street. Through the power of the internet, they unknowingly fall for each other after meeting on an online chat room. 

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Crazy Rich Asians (2018)

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New York University professor Rachel Chu (Constance Wu) agrees to accompany her boyfriend Nick Young (Henry Golding) on his trip back home to Singapore for his best friend’s wedding. Only when she reunites with her roommate from college does she realize the enormity of the Young family’s celebrity and how the wedding is actually the social event of the century.   

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13 Going on 30 (2004)

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13 Going on 30 had us all wishing to be “Thirty, Flirty and Thriving” (in the beginning). From the killer 80s soundtrack to the bitchin wardrobe to the unforgettable scene where Jenna (Jennifer Garner) livens up the launch party by performing the iconic zombie dance, you can’t go wrong with this feel-good flick. Plus, the razzles. 

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Notting Hill (1999)

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Julia Roberts and Hugh Grant take center stage in this classic 90s romantic comedy about a Hollywood A-Lister who falls for a humble bookstore owner in an affluent neighborhood in London. 

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When Harry Met Sally (1989)

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A relatable story about two people who strike up an unlikely friendship that leads them to question whether a man and a woman can be just friends. With a boatload of memorable moments and hilarious scenes, When Harry Met Sally is the perfect flick to satisfy that rom-com itch. 

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10 Things I Hate About You (1999)

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This adaptation of Shakespeare’s “The Taming of the Shrew” is a quintessential 90s rom-com, featuring a star-studded cast: Julia Stiles, Heath Ledger, Joseph Gordon-Levitt, Larisa Romanovna Oleynik, Gabrielle Union, Andrew Keegan and more. With its heartwarming life lessons, some beautiful sisterly bonding and Kat’s iconic monologue at the end, 10 Things I Hate About You is the perfect romantic comedy for your weekend movie marathon (or weekday, whatever floats your boat).    

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