Must-See Romantic Movies
Romantic Movies 101
It’s a classic formula: two people meet, they fall in love, and they live happily ever after… most of the time. Since the early days of Hollywood, romantic dramas and comedies have been blockbuster hits, some lasting decades as new generations fall in love with the characters and their stories. Whether you’re in need of a Valentine’s Day gift, you’re planning a romantic evening in, or you’re adding to your collection, these classics are must-haves and must-watches for any romantic movie buff.
Gone with the Wind (1939)
This epic drama follows the turbulent life and love affairs of the beautiful Southern belle, Scarlett O’Hara. It’s the eve of the American Civil War, and Scarlett is on the verge of losing the man she has always loved, Ashley Wilkes, who is engaged to another woman. Though Scarlett pines over Ashley, Rhett Butler, the handsome blockade runner and societal outsider, pursues Scarlett. Through the turmoil of the American Civil War, Scarlett loses the man she loves, and comes to conclusions about life and love too late.
Casablanca is the story of lovers torn apart during World War II, then brought together again by chance, and forced to choose between love or safety. The story is set in Casablanca in 1941, where Rick Blaine, a handsome American expatriate, owns an upscale bar that is frequented by Europeans hoping to escape to America. One night, his former lover, Ilsa Lund, walks into the bar with her husband — the man for whom she left Rick. Tensions run high as danger mounts, and it becomes apparent that the love affair between Ilsa and Rick isn’t quite over. Rick must choose between running away with Ilsa, or sending her to safety with her husband.
The Way We Were (1973)
Set shortly after World War II, this bittersweet love story starts with a flashback to when Katie Morosky and Hubbell Gardiner were attending the same college. They’re from two different worlds — she’s a staunch political activist, and he’s a popular jock with few cares in the world. She’s attracted to his boyish good looks and talent for writing, and he’s intrigued by her steadfast beliefs and views of the world. They never act on their attraction to one another, until years later after Hubbell returns from war. They quickly become a passionate but unlikely pair — she’s devoted to her strong political views, and he’s fallen into a career and social circle that he loves, but is the opposite of everything she stands for. Though their love is strong, they realize they’re holding each other back from being the people they want to be.
Dirty Dancing (1987)
It’s the summer of 1963, and Frances “Baby” Houseman is vacationing with her family at a resort in the Catskill Mountains. She meets the resort’s dance instructor and leader of the resort’s entertainment staff, Johnny Castle. One night, Baby sees Johnny and the other staff at a secret after-hours work party, where everyone is “dirty dancing”. The dancing captivates Baby, and Johnny offers to teach her a few moves. Soon after, Baby fills in for Johnny’s dance partner, and they start a secret love affair. As rumours circulate and drama builds at the resort, Baby and Johnny must stand up for themselves and their love.
It’s a supernatural story of love overcoming death. Sam Wheat and Molly Jensen are an average couple in New York City; he’s a banker, she’s a potter, and they’re completely in love with one another. One night, on the way home from a date, Sam is murdered in what seems to be a random attack. He quickly realizes that he’s dead, but his ghost is still on earth. Soon, he learns that his death wasn’t an accident, and that Molly is also in danger. Sam stays close to Molly as he desperately tries to communicate with her to keep her safe.
It’s a timeless story of star-crossed lovers, Rose DeWitt Bukater and Jack Dawson. 84 years after the sinking of the Titanic, Rose tells the story she’s never shared: of her fleeting romance on board the Titanic, and how it changed her life. He was a poor artist on an adventure, and she was a socialite engaged to a wealthy man, trapped in a life that she didn’t want. The two met in a chance encounter on the ill-fated voyage, and began a fiery romance after he saved her life. Their love affair was cut tragically short when the ship hit an iceberg, but the course of her life was already forever changed.
A Walk to Remember (2002)
In this classic coming-of-age story, two teenagers meet and fall in love, despite their differences. Set in the late 1990s in North Carolina, Landon Carter, a popular and rebellious teen, gets in trouble with the law and is forced to take part in after-school community service. It’s there that he meets Jamie Sullivan, the quiet and bookish reverend’s daughter. Jamie and Landon begin to spend most of their time together, and soon they fall in love — much to the dismay of his popular friends and her strict father. Their relationship is put to the test when she reveals that she’s been keeping a big secret — one that will alter the course of their romance, and change him forever.
The Notebook (2004)
This timeless love story begins in 1940 in a small town in South Carolina, and follows the summer romance of Noah Calhoun and Allie Hamilton. He’s smitten from the moment he sees her — but he’s a working-class boy from humble beginnings, and she’s a rich girl with the world at her feet. Though he’s poor, he’s passionate and gives her a sense of freedom that she’s never had. Her parents strongly disapprove of their love affair, and they ban her from seeing him with hopes that she’ll get over her summer romance and marry someone of her status. Years later, fate intervenes, and Allie is forced to choose between the man that can offer a lifetime of comfort and class, and the man she has always loved.
Pride & Prejudice (1995 and 2005)
Based on the beloved novel by Jane Austen, the story of Elizabeth Bennet and Mr. Darcy was first published in 1813. This timeless story of status, society, and overcoming one’s prejudices has lived on for 200 years, passed down and adored by generations. When Elizabeth first meets Mr. Darcy, he’s an eligible bachelor who makes a strong first impression: he’s arrogant and obnoxious, and believes he’s too good for her. As time goes by, he finds himself increasingly attracted to her, and she starts to see another side of him. Set in a time when reputation and social standing meant everything, their budding romance is plagued by drama, misconceptions, and the pride that can hold someone back from pursuing what they truly want.
The Princess Bride (1987)
In this classic fairytale with a few twists, the beautiful Buttercup is engaged to the repulsive Prince Humperdinck. On the eve of their wedding, a trio of outlaws kidnap Buttercup in a plot schemed up by the cunning Prince. It’s a story of love and adventure, as Buttercup’s childhood sweetheart, Westley — who she believed to be dead — comes to her rescue. Before long, Prince Humperdinck catches up with Buttercup and Westley, and takes Westley as a prisoner. If Buttercup marries the Prince, he’ll spare Westley — but the Prince hasn’t told the full truth, and Westley is in grave danger. Through many twists and turns, the story of Buttercup and Westley ends as all fairy tales do — happily ever after.
When Harry Met Sally (1989)
It’s an unconventional love story with one big question: can men and women ever be just friends? Their story starts after college graduation, when acquaintances Harry Burns and Sally Albright road trip from Chicago to New York to start their post-grad lives. Over the course of the trip, they discuss their different philosophies on men, women, and relationships, and draw one big conclusion: they can never be friends. Once in New York, they go their separate ways and get on with their lives. Over the course of the next 10 years, they’re reunited in chance encounters and always pick up where they left off, bickering about the nature of relationships between men and women. Soon enough, their friendship grows, and after a few failed romances and plenty of quarrels, Harry and Sally start to accept their quirky relationship for what it truly is.
Pretty Woman (1990)
In this grown-up Cinderella story, Vivian Ward, a young woman who’s desperate to make rent, is hired by Edward Lewis, a wealthy man who pays her $3,000 to be his date at social and work events for the week. They’re an unlikely pair; she’s beautiful, bold, and broke, and he’s a successful and ruthless businessman. Over the course of the week, Edward begins to fall for her, and she feels the same for him. They keep their arrangement a secret from Edward’s business partners and colleagues, but their romance begins to unravel when rumours spread about Vivian’s life. He can give her a life in the lap of luxury, but is it the fairy tale that she wants?
Sleepless in Seattle (1993)
Sam Baldwin, an architect from Chicago, has recently lost his wife, Maggie. A year and a half after Maggie dies, Sam’s son, Jonah, wants him get his life back together, and he thinks a new wife will bring Sam back to the man he once was. To help Sam move on, Jonah calls into a radio show to force Sam to talk about his grief. Women all across America are touched by Sam’s story, including Annie Reed, a reporter for the Baltimore Sun. Despite being engaged, Annie can’t stop thinking about Sam, and despite Jonah’s persistence, Sam isn’t quite ready to move on — but a serendipitous meeting and Jonah’s determination give Sam and Annie a second chance at love.
You’ve Got Mail (1998)
She hates him. He hates her. It's the dog-eat-dog world of business. Her name is Kathleen Kelly and his, Joe Fox. They're rival bookstore owners but little do they know that their real life strife is more complex — they’re good friends on the internet. As “NY152” and “Shopgirl”, they meet in a chat room, share their stories of how much they love Manhattan, muse about custom-made espresso drinks, and talk about other subjects of the day via a dial-up internet connection. Here’s the real-life challenge: he’s opening his giant bookstore, a modern-day piazza where you can get a cappuccino with a copy of the latest bestseller, just around the corner from her children’s bookstore, founded by her deceased mother. How will their budding internet romance and competing businesses work out?
Notting Hill (1999)
Will Thacker is just an average guy with a failing business, a weird roommate, and a divorce under his belt, and Anna Scott is the most famous movie star in the world. Even though they’re from different worlds, sparks fly when she walks into his bookshop in Notting Hill, a trendy neighourhood in London. Together, they navigate the difficulties of Anna’s private life when she lives in the spotlight, and they struggle to create an ordinary relationship as Will learns that fame isn’t all it appears to be, and being with the world’s most-loved woman isn’t easy.
10 Things I Hate About You (1999)
Based on Shakespeare’s comedy, The Taming of the Shrew, this story follows the problematic relationships between Bianca Stratford, a popular high school student, her outcast older sister Kat, who is irritable on the best days, and the boys stuck in the middle. Cameron, the new kid in school, wants to take Bianca on a date, but there’s a catch: Bianca isn’t allowed to date unless Kat is also in a relationship. Cameron schemes with the popular rich kid, Joey, who also wants to date Bianca, and together they create a plan: Joey will pay the ill-tempered outsider Patrick to take Kat out, and Bianca will be free. But is it worth the cost?
Bridget Jones’s Diary (2001
Bridget Jones is an average 30-something woman who’s battling her weight, her vices, and her lackluster love life. As a New Year’s resolution, she starts keeping a diary in an attempt to be honest about her life and to turn things around. Suddenly she’s a woman torn between two men — the hopelessly charming Daniel Cleaver, and Mark Darcy who is... not as charming. Bridget stumbles through the highs and lows of her relationships, and though she never handles her exploits with grace or dignity, she comes out on top, yet still fabulously flawed.
Love, Actually (2003)
Set in London over the holiday season, it’s the story of love and the many complications of relationships; sometimes it’s with the right person, sometimes it’s with the wrong person, sometimes it’s hard to say exactly how you feel or what you want, and sometimes it’s said a moment too late. Told through intertwined stories of Londoners falling in and out of love, it’s stories of love at all ages and stages: innocent young love, budding romances, broken hearts, and the temptations that can scar a relationship. As the characters work through their relationships, it’s unmistakable that “love actually is all around.”
50 First Dates (2004)
What do you do when the woman you love doesn’t remember who you are? If you’re Henry Roth, you recreate the moment you met, each and every day, with hopes that she’ll eventually remember. After a bad car accident left Lucy Whitmore with amnesia, she wakes up every morning thinking it’s October 13, 2002, with no recollection of anything that’s happened since the accident. When Harry meets her at a café, they hit it off and agree to meet again the next day — except Lucy doesn’t remember who he is. Day after day, Harry tries to recreate their meeting, hoping she’ll remember him. Harry begins to fall in love with Lucy, and even though she never remembers meeting him, Harry never stops trying to win her over.
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