I’m Sick Of Watching Movies That Glorify Women Choosing Their Careers Over A Loving Relationship—Here Are 15 Classics That Never Disappoint

Many modern movies prioritize independence over romance.

By Meghan Dillon4 min read
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Camilla Cabello’s Cinderella is a prime example of modernity’s imposed (and false) dichotomy of a man or a career. And the upcoming live-action remake of Snow White, starring Rachel Zegler, is promising to follow suit, as Zegler has stated, "She's not gonna be saved by the prince and she's not going to be dreaming about true love.” But, contrary to popular belief, women can have the career and the guy, and it’s also okay if she decides that her relationship is more important than her job.

I miss the old days when couples ended up together happily at the end of movies. Here are some of my favorite romantic movies with happy endings.

1. Breakfast at Tiffany’s (1961)

This Audrey Hepburn classic is an unconventional romantic comedy, but it’s iconic for a reason. Holly Golightly (Audrey Hepburn) is one of the most charming characters to ever grace the silver screen. She’s a quirky and naive socialite, and Paul (George Peppard) is her handsome new neighbor who inevitably falls for her. As Holly’s past comes back to haunt her, Paul helps her realize that she’s worthy of love. Whether you watch it for the fashion or for the love story, it’s impossible to get tired of this movie.

2. How To Lose a Guy in 10 Days (2003)

Though Andie and Ben didn’t start with a healthy relationship (it’s kind of the whole point of the movie), the fact that Andie ends up getting the job she wants and gets the guy is enough to put this movie on this list (not sorry for spoiling, it’s your fault if you haven’t seen it yet). It’s also a classic romantic comedy, and it’s impossible to go wrong with picking this movie.

3. Clueless (1995)

Based on Emma by Jane Austen, Clueless tells the story of Cher Horowitz (Alicia Silverstone) and her hilarious friends as she tries to play matchmaker, only to annoy her handsome ex-stepbrother (Paul Rudd). Though it’s made for teenagers, women (and men with taste) of all ages can enjoy and laugh with this wholesome classic.

4. Pride and Prejudice (2005)

Yes, we’re calling it – the 2005 version of Pride and Prejudice with Keira Knightley as Elizabeth Bennett and Matthew Macfadyen as Mr. Darcy is the best film adaptation. This version does a great job showcasing the comedic aspect of Jane Austen’s classic novel, leaving us laughing as much as we’re swooning over this timeless love story.

5. A Cinderella Story (2004)

All Sam (Hilary Duff) wants to do is escape the clutches of her stepmother (Jennifer Coolidge) and attend Princeton for college. High school football star Austin (Chad Michael Murray) wants to pursue writing over football, but he doesn’t know how to tell his father. The two meet in a chat room only to discover that they go to the same school, and the sequence of events coincidentally resembles one of our favorite fairy tales.

6. Notting Hill (1999)

We had to honor the queen of rom-coms, Julia Roberts, with one of her best romantic comedies. Bookstore owner William (Hugh Grant) meets famous actress Anna Scott (Julia Roberts) on a whim, and they subsequently fall for each other. It’s definitely on the cheesy side, but we guarantee it will fill your heart with joy.

7. Grease (1978)

In this classic musical, good girl Sandy (Olivia Newton-John) falls for bad boy Danny (John Travolta) during summer vacation, only to discover that he wasn’t who she thought he was when the school year begins. While Danny spends the rest of the year trying to win her back, the two realize that sometimes it’s okay to change for love.

8. 13 Going On 30 (2004)

Who doesn’t love a rom-com with Jennifer Garner? 13-year-old Jenna (Jennifer Garner) wishes to fast-forward to 30, only to wake up one morning to find her dream come true. The dream quickly turns into a nightmare when she finds her childhood best friend Matty (Mark Ruffalo) and learns that she had to pay a hefty price for her dreams to come true. This feel-good comedy reminds us to always embrace our inner child, and it never gets old.

9. Gentlemen Prefer Blondes (1953)

A little-known fact about Marilyn Monroe is that she was hilarious. Showgirls Lorelei (Marilyn Monroe) and Dorothy (Jane Russell) go on a cruise to France, only for Dorothy to fall for Ernie (Elliott Reid), a man who was hired to spy on Lorelei. From hilarious hijinks to Marilyn’s iconic performance of “Diamonds Are a Girl’s Best Friend,” this movie is considered a classic for a reason.

10. When Harry Met Sally (1989)

Some make fun of this movie for being too predictable and cliché, but that’s what makes it one of the best romantic comedies ever made. The movie follows Harry (Billy Crystal) and Sally (Meg Ryan) over the course of their friendship for several years before they eventually get together. The movie asks if men or women can truly be just friends, and we can never get enough of watching the two of them fall in love.

11. Legally Blonde (2001)

After her boyfriend dumps her, Elle Woods (Reese Witherspoon) decides to go to Harvard Law to win him back. When she discovers that he’s engaged to another woman, Elle decides to work her butt off in law school to prove him wrong, only to discover that she’s a talented lawyer. She also catches the eye of another handsome law student (Luke Wilson) and gets everything she wants and more at the end.

12. Meet Me in St Louis (1944)

This Judy Garland classic follows a family in early 20th-century St. Louis who are excited for the upcoming World’s Fair, only to discover that their father has a job offer in New York City. As Christmas draws closer, the family realizes how much St. Louis really means to them.

13. Bringing Up Baby (1938)

It’s impossible to go wrong with a movie starring two all-time greats like Cary Grant and Katharine Hepburn. David (Cary Grant) is a paleontologist on the edge of a discovery that can make his career and is engaged to marry a woman who can make it happen. Shortly before his wedding, he meets Susan (Katharine Hepburn), and the two embark on various adventures to help him make his discovery. It’s as heartwarming as it is hilarious, making this a feel-good classic.

14. It Happened One Night (1934)

The oldest movie on this list, Clark Gable and Claudette Colbert star in one of the world’s first romantic comedy films, and it’s one of the best. Ellen (Claudette Colbert) and Peter (Clark Gable) fall in love after a series of adventures (and some misadventures) that will have you laughing until the end. 

15. 10 Things I Hate About You (1999) 

Loosely based on William Shakespeare’s The Taming of the Shrew, Bianca (Larisa Oleynik) can’t date until her rebellious older sister, Kat (Julia Stiles), does. This inspires Bianca’s crush, Cameron (Joseph Gordon-Levitt), to convince bad boy Patrick (Heath Ledger) to date Kat, who falls in love with her for real along the way. It’s as cliché as it is cute, and the iconic poem Kat recites at the end will no doubt fill your eyes with tears.

Closing Thoughts

From Old Hollywood classics like It Happened One Night to early 2000s rom-coms like How To Lose a Guy in 10 Days, there are plenty of classics that prioritize romance over anything else. There are some movies where the woman *gasps* gets the career and the guy, proving that women can have both and live happily ever after.

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