Romantic Comedies That Stand the Test of Time

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Rewatching the same films often has a soothing effect. Watching something you've seen before provides a sense of familiarity and nostalgia, which is comforting, especially during challenging or uncertain times. Seeing the same film again also helps you reconnect with the characters, storylines, and emotions. It's like revisiting old friends!

Why We Love Rewatching Rom-Coms

According to cognitive psychologist Robert Kraft, Ph.D., "When rewatching familiar shows, we receive the stories and emotions we expect. We know how the episodes end and — more importantly — how we’ll feel when they end. Which is one reason we’re more likely to choose comedies for repeated viewing instead of dramas or tragedies."

Whip out your favorite rom-coms to watch during a time you need a pick-me-up, or try one of these timeless films to get hooked on a new favorite!

'90s Timeless Rom-Coms

Romantic comedies from the '80s and '90s sparkle with a timeless charm and have become beloved classics. During this era, these films delighted audiences with witty humor, memorable characters, and heartwarming love stories.

  • Notting Hill is a charming tale of a bookstore owner who falls in love with a famous actress after a chance encounter in London's Notting Hill neighborhood.

  • Pretty Woman is an iconic film that follows the unlikely love story between a wealthy businessman and a vivacious prostitute in Los Angeles.

  • 10 Things I Hate About You, a modern retelling of Shakespeare's The Taming of the Shrew, follows the romantic entanglements of high school students.

  • Sleepless in Seattle tells the heartwarming story of a widowed man's son who calls a radio talk show in an attempt to find his father a partner.

  • You've Got Mail features business rivals who hate each other at the office but fall in love over the internet, unaware of each other's true identity.

  • Four Weddings and a Funeral follows the romantic misadventures of Charles, who falls for a woman he keeps running into at, you guessed it, four weddings and a funeral.

  • While You Were Sleeping features Sandra Bullock as a lonely ticket-taker who saves her crush, a man she only views from afar, from an oncoming train. While he's in a coma, a misunderstanding causes his family to believe she's his fiancée.

  • Chasing Amy is an unconventional romantic comedy that tells the story of a man who falls in love with a lesbian

2000s Romantic Comedies

The 2000s was an exceptional era for romantic comedies. These films were known for tender, loving scenes and dreamy romance. They're worth rewatching countless times!

  • How To Lose a Guy in 10 Days features a journalist who bets she can make a man fall in love with her in 10 days, while the man she chooses for the experiment has his own agenda.

  • The Notebook is a young couple's love story narrated by an old man to an elderly woman with dementia, as he reads from a faded notebook.

  • Ghosts of Girlfriends Past tells the story of a womanizer attending his brother's wedding, where he's visited by the ghosts of his past girlfriends, making him question his commitment issues.

  • A Walk to Remember follows a high school rebel and a shy, religious girl as they fall in love, but their relationship faces a test when tragedy strikes.

  • A Cinderella Story is a modern retelling of the classic Cinderella tale, where a teenage girl finds love with a popular boy through a series of text messages and encounters at a school dance.

  • 50 First Dates tells the story of a man who falls in love with a woman who has short-term memory loss and must find a way to make her fall in love with him every day.

  • The Proposal revolves around a high-powered executive who forces her assistant to marry her in order to avoid deportation to Canada, but the fake engagement eventually leads to unexpected feelings.

  • It's Complicated features a divorced couple reigniting their romance during a family gathering, leading to a complex love triangle involving their new partners.

Rom-Coms From the 2010s

Rom-coms of this era take a sillier approach than those from past decades. Enjoy a love story with obvious, relieving humor throughout. The touch of wit combined with modern dating styles makes these stories more relatable but less nostalgic.

  • Knight and Day is a romantic action-comedy film. It follows the story of a woman who becomes involved with a mysterious man on a whirlwind adventure, unaware of his true identity.

  • Valentine's Day intertwines the lives of several characters in Los Angeles as they navigate love and relationships on Valentine's Day. The film features an ensemble cast and explores various romantic storylines.

  • New Year's Eve follows the lives of several characters in New York City on New Year's Eve. The movie explores love, new beginnings, and the idea of making resolutions for the upcoming year.

  • Crazy Rich Asians, based on the bestselling novel, follows a young Asian-American woman who accompanies her boyfriend to Singapore to meet his wealthy family. The film showcases the clash between traditions, social status, and modern love.

  • The Other Woman features three women who become unlikely friends after discovering that they are all involved with the same cheating man. Together, they embark on a humorous revenge plan.

  • Friends with Benefits explores the complexities of a casual, no-strings-attached relationship between two friends who find themselves falling in love.

  • Crazy, Stupid, Love follows the intertwining lives of various characters as they navigate love, infidelity, and self-discovery.

Strong Female Leads

These movies, mostly from the 2000s, are officially rom-coms but focus a bit more on the journey of a strong female main character. Enjoy an empowering story of self-discovery with a romantic side journey.

  • Burlesque is a musical romantic drama film that follows the story of a small-town girl who moves to Los Angeles and becomes a performer at a neo-burlesque club.

  • Mamma Mia! centers around a bride-to-be who invites three men from her mother's past to her wedding in the hopes of figuring out who her father is. It's a fun-filled film with lots of hit songs from the band ABBA.

  • He's Just Not That Into You explores the complexities of modern dating and the different ways people interpret romantic signals.

  • Eat Pray Love tells the true story of a woman who goes on a journey of self-discovery after a painful divorce. She travels to Italy, India, and Bali, where she finds love, spirituality, and inner peace.

  • Miss Congeniality follows the story of an FBI agent who goes undercover as a contestant in the Miss United States beauty pageant to prevent a terrorist attack. Along the way, she learns about personal growth, friendship, and embracing one's true self.

  • Because I Said So is about a meddling mother who tries to find the perfect man for her youngest daughter. She secretly sets up an online dating profile and interviews potential suitors without her daughter's knowledge.

Reminisce With a Rom-Com

Whether you choose to revisit these beloved classics or discover new favorites, these romantic comedies stand the test of time and provide endless enjoyment for viewers of all ages. Grab your popcorn, settle in, and let these films whisk you away into a world of love, laughter, and happy endings.

If you're a sucker for rom-coms, get ready for a new kind of experience. Netflix announced their upcoming interactive rom-com production, Choose Love, airing in August 2023. Get ready to choose your own romantic storyline!

For more advice on harnessing your romantic side or entertainment recommendations, subscribe to Cupid's Light.

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