The 52 Best Rom-Com Movies

50 Best Rom-Com Romantic Comedies

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Before we list the 50 best rom com movies, we want to see how well YOU know your Romantic comedies!

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Our 50 Favorite Rom-Com Movies

Without further ado, and in no particular order (because let’s face it, they’re all great!) here is a list of the 50 best favorite rom-com movies of all time. Think we missed one? Let us know in the comments section below!

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Pretty Woman (1990)

In this modern update on Cinderella, a prostitute and a wealthy businessman fall hard for one another, forming an unlikely pair.

13 Going on 30 (2004)

After total humiliation at her thirteenth birthday party, Jenna Rink wants to just hide until she’s thirty. Thanks to some wishing dust, Jenna’s prayer has been answered.

Doc Hollywood (1991)

A young doctor on his way across the country to a job interview crashes his car in a small town and is sentenced to work for several days at the town hospital. All he wants is to serve the sentence, get his car fixed and get moving, but gradually the locals become attached to the new doctor.

Love Actually (2003)

Follows the lives of eight very different couples in dealing with their love lives in various loosely interrelated tales all set during a frantic month before Christmas in London, England.

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10 Things I Hate About You (1999)

Adapted from William Shakespeare’s play “The Taming of the Shrew,” Kat is beautiful, smart and quite abrasive to most of her fellow teens, meaning that she doesn’t attract many boys. Unfortunately for her younger sister Bianca, house rules say that she can’t date until Kat has a boyfriend. Strings are pulled to set the dour damsel up for a romance.

You’ve Got Mail (1998)

Book superstore magnate Joe Fox and independent book shop owner Kathleen Kelly fall in love in the anonymity of the Internet, both blissfully unaware that he’s trying to put her out of business.

Hitch (2005)

Dating coach Alex “Hitch” Hitchens mentors a bumbling client Albert, who hopes to win the heart of the glamorous heiress. While Albert makes progress, Hitchens faces his own romantic setbacks when proven techniques fail to work on Sara Melas, a tabloid reporter digging for dirt on Allegra Cole’s love life.

Definitely, Maybe (2008)

Will Hayes, a 30-something Manhattan dad is in the midst of a divorce when his 10-year-old daughter, Maya, starts to question him about his life before marriage. Maya wants to know absolutely everything about how her parents met and fell in love.

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

Lara Jean Covey writes letters to all of her past loves, the letters are meant for her eyes only. Until one day when all the love letters are sent out to her previous loves. Her life is soon thrown into chaos when her foregoing loves confront her one by one.

My Big Fat Greek Wedding (2002)

Toula Portokalos is 30, Greek American, and works in her family’s restaurant. All her father Gus wants is for her to get married to a nice Greek boy. After her mother convinces Gus to let her take some computer classes at college, she then takes over her aunt’s travel agency where she meets Ian Miller. Ian is a high school English teacher and an absolute dreamboat.

Sleepless in Seattle (1993)

A recently widowed man’s son calls a radio talk-show in an attempt to find his father a partner.

Yesterday (2019)

A struggling musician realizes he’s the only person on Earth who can remember The Beatles after waking up in an alternate reality where they never existed.

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Pretty in Pink (1986)

A poor girl must choose between the affections of dating her childhood sweetheart or a rich but sensitive playboy.

Singles (1992)

A group of twenty-something friends search for love and success in grunge-era Seattle.

Bridget Jones’s Diary (2001)

Bridget decides to take control of her life, starting by keeping a diary which she always tell the complete truth. The fireworks begin when her charming though disreputable boss takes an interest in the quirky Miss Jones. Thrown into the mix are Bridget’s band of slightly eccentric friends and a rather disagreeable acquaintance into whom Bridget cannot seem to stop running or help to find quietly attractive.

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Clueless (1995)

Cher, a high school student in Beverly Hills, must survive the ups and downs of adolescent life. Her external demeanor at first seems superficial, but rather it hides her wit, charm, and intelligence which help her to deal with relationships, friends, family, school, and the all-important teenage social life.

Sweet Home Alabama (2002)

A young woman who has reinvented herself as a New York City socialite must return home to Alabama to obtain a divorce from her husband after seven years of separation. She comes to realize what she had in the south was far more perfect than her New York City life.

Sixteen Candles (1984)

Samantha’s life is going downhill fast. The 16-year-old has a crush on the most popular boy in school, and the geekiest boy in school has a crush on her. Her sister is getting married, and with all the excitement the rest of her family forgets her birthday. Add to all this two sets of horrendously embarrassing grandparents, a foreign-exchange student named Long Duk Dong, and behold the makings of a hilarious journey into young-womanhood.

Notting Hill (1999)

The life of a simple bookshop owner changes when he meets the most famous film star in the world.

Miss Congeniality (2000)

An F.B.I. Agent must go undercover in the Miss United States beauty pageant to prevent a group from bombing the event.

Jerry Maguire (1996)

When a sports agent has a moral epiphany and is fired for expressing it, he decides to put his new philosophy to the test as an independent agent with the only athlete who stays with him and his former colleague.

Forgetting Sarah Marshall (2008)

Devastated Peter takes a Hawaiian vacation in order to deal with the recent break-up with his TV star girlfriend. Little does he know, Sarah’s traveling to the same resort as her ex – and she’s bringing along her new boyfriend.

Chasing Amy (1997)

A pair of comic book authors, who live in New Jersey, have been best friends for 20 years. They spend their time working in their studio, and in the evenings they are going out. But their friendship is about to be disputed for the first time in their lives when a beautiful young lesbian woman named Alyssa Jones enters their life and Holden falls in love with her. Now Holden has to deal with Banky’s jealousy, and with his new girlfriend’s very rich past.

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Breakfast at Tiffany’s (1961)

A young New York socialite becomes interested in a young man who has moved into her apartment building. Hardship arises when her past threatens to get in the way.

When Harry Met Sally (1989)

Harry and Sally have known each other for years, and are very good friends, but they fear sex would ruin the friendship.

Knocked Up (2007)

For fun-loving party animal Ben Stone, the last thing he ever expected was for his one-night stand to show up on his doorstep eight weeks later to tell him she’s pregnant with his child.

Bridesmaids (2011)

Competition between the maid of honor and a bridesmaid, over who is the bride’s best friend, threatens to upend the life of an out-of-work pastry chef.

Shakespeare in Love (1998)

The world’s greatest-ever playwright, William Shakespeare, is young, out of ideas and short of cash. He meets his ideal woman and is inspired to write one of his most famous plays.

silver linings playbook

Silver Linings Playbook (2012)

After a stint in a mental institution, former teacher Pat Solitano moves back in with his parents and tries to reconcile with his ex-wife. Things get more challenging when Pat meets Tiffany, a mysterious girl with problems of her own.

The Princess Bride (1987)

While home sick in bed, a young boy’s grandfather reads him the story of a farmboy-turned-pirate who encounters numerous obstacles, enemies and allies in his quest to be reunited with his true love.

Crazy Rich Asians (2018)

This contemporary romantic comedy, based on a global bestseller, follows native New Yorker Rachel Chu to Singapore to meet her boyfriend’s family.

She’s All That (1999)

A high school jock makes a bet that he can turn an unattractive girl into the school’s prom queen.

27 Dresses (2007)

After serving as a bridesmaid 27 times, a young woman wrestles with the idea of standing by her sister’s side as her sibling marries the man she’s secretly in love with.

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The Proposal (2009)

A pushy boss forces her young assistant to marry her in order to keep her visa status in the U.S. and avoid deportation to Canada.

How to Lose a Guy in 10 Days (2003)

Benjamin Barry is an advertising executive and ladies’ man who, to win a big campaign, bets that he can make a woman fall in love with him in 10 days.

John Tucker Must Die (2006)

Three ex-girlfriends of a serial cheater set up their former lover to fall for the new girl in town. Together, they make a plan to watch him get his heart broken.

She’s The Man (2006)

When her brother decides to ditch for a couple of weeks, Viola heads over to his elite boarding school, disguised as him, and proceeds to fall for his school’s star soccer player. She soon learns she’s not the only one with romantic troubles.

A Lot Like Love (2005)

Unacquainted Emily and Oliver join the mile-high club together on the way from LAX to NYC–end of story. Except that they keep meeting constantly over the next seven years.

Chasing Liberty (2004)

Anna Foster has never had an ordinary life. At eighteen years old, she is the most protected girl in America; she is the First Daughter. Frustrated with her overprotective father, Anna makes a deal with him: only two agents are allowed to guard her while at a concert in Prague. When her father backs out of his promise, Anna goes on the run.

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Girls Trip (2017)

Four lifelong friends travel to New Orleans for the annual Essence Festival. Sisterhoods are rekindled, wild sides are rediscovered, and there’s enough dancing, drinking, brawling and romancing to make the Big Easy blush.

Coyote Ugly (2000)

Songwriter Violet, gets a job at a women-run NYC bar that teases its male patrons, comes out of her shell.

Sex and the City (2008)

In this classic rom com movie, four female New Yorkers gossip about their sex lives (or lack thereof) and find new ways to deal with being a woman in the late 1990s.

The Other Woman (2014)

After discovering that her boyfriend is married, Carly meets the wife he’s been betraying. When yet another affair is discovered, all three women team up to plot revenge on the three-timing S.O.B.

Working Girl (1988)

When a secretary’s idea is stolen by her boss, she seizes an opportunity to steal it back by pretending she has her boss’ job.

friends with benefits movie

Friends With Benefits (2011)

A young man and woman decide to take their friendship to the next level without becoming a couple. They soon discover that adding sex only leads to complications.

Two Night Stand (2014)

A snowstorm forces two people who made an online connection to unwillingly extend their one-night stand.

About Last Night (2014)

Follow two couples as they journey from the bar to the bedroom and are eventually put to the test in the real world.

The Kissing Booth (2018)

Elle is a pretty late-bloomer who’s never-been-kissed, decides to run a kissing booth at her high school’s Spring Carnival, she unexpectedly finds herself locking lips with her secret crush.

Bend it Like Beckham (2002)

Two ambitious girls, despite their parents’ wishes, have their hearts set on careers in professional football.

What is a Duff

The Duff (2015)

A high school senior instigates a social pecking order revolution after finding out that she has been labeled the DUFF – Designated Ugly Fat Friend – by her prettier, more popular counterparts

Palm Springs (2022)

Stuck in a time loop, two wedding guests develop a budding romance while living the same day over and over again.

The Hating Game (2021)

Resolving to achieve professional success without compromising her ethics, Lucy embarks on a ruthless game of one-upmanship against cold and efficient nemesis Joshua, a rivalry that is complicated by her growing attraction to him. The Hating Game is based on a best-selling novel by Sally Thorne

How many of our top 50 best rom-com movies have you watched? And how many have you watched more than once!? No shame, us too! Not sure how to catch up on some of these classics? We recommend Amazon Prime, they have a fantastic list of old and new romantic comedies!

There are SO MANY other great rom-com movies that didn’t make our list. Leave any of your favorites that we missed in the comments below and we’ll get started on a top 100 list!

The best rom com movies to watch this Valantines Day
Kim Dow Sass Magazine

Kim is the owner and publisher of Sass Magazine, as well as the owner of Sass Studios, a boutique graphic design studio in Frederick, MD. When not in the office, Kim can be found doing some of her favorite hobbies—reading a book, dancing, traveling, or playing with her rescued pitbull.

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