Boomers Found These 10 Rom-Coms Romantic, Millennials Disagree

Photo of author
Written By Amanda Anthony

Amanda is a freelance writer passionate about horror and fantasy films. When she’s not writing about the latest celebrity hijinks and epic on-screen moments, you can find her watching Blumhouse films through the delicate fibers of a protective blanket. Amanda lives in Halifax, Nova Scotia, with her husband, kiddos, and goofy golden doodle, Ripley.

Rom-coms make us feel good. They’re like a cozy blanket with dependable storylines, likable characters, and happy endings. Or, at least most of them are.

But, some rom-coms miss the mark, leaving a bad taste in the mouth. Here are 10 rom-coms that may have seemed romantic when they were made, but modern audiences think they weren’t so romantic after all.

Breakfast at Tiffany’s (1961)

Rom Coms
Image Credit: Paramount Pictures

Breakfast at Tiffany’s is a cult classic. Too bad the film aged so poorly. The film stars Audrey Hepburn (My Fair Lady) as New York socialite Holly Golightly, and George Peppard (The Blue Max) as her new neighbor, Paul Varjak. Golightly is looking for a rich man to marry, and Varjak fits the bill. Along with the “gold-digger” theme, the film carries nasty racist overtones. Mickey Rooney (Babes in Arms) plays the upstairs neighbor, Mr. Yunioshi, portraying offensive Asian stereotypes that today’s audiences wouldn’t accept.

Sixteen Candles (1984)

Rom Coms
Image Credit: Universal Pictures

Sixteen Candles poses the comedic premise of a family forgetting their daughter’s sixteenth birthday. High school hijinks ensue. Cute right? Not so much. The film might feature 80’s movie sweetheart Molly Ringwald (The Breakfast Club), but it’s full of offensive Asian stereotypes. Baker’s romantic interest, Jake Ryan (Michael Schoeffling), also makes some gross comments that don’t jive with the way a modern audience values consent. Not so romantic.

Overboard (1987)

Rom Coms
Image Credit: Metro-Goldwyn-Mayer

Goldie Hawn (The First Wives Club) and Kurt Russel (The Hateful Eight) star as a wealthy socialite and small-town handyman. After firing Dean Proffit (Russel), Joanna (Hawn) falls overboard and wakes up with amnesia. Proffit hatches a plan to make her believe she’s his wife and take care of his four children. The two fall in love, despite his lying to her and allowing his children to manipulate her. How romantic…not.

Sleepless in Seattle (1993)

Rom Coms
Image Credit: TriStar Pictures

Meg Ryan (Kate and Leopold) and Tom Hanks (A League of Their Own) star as Annie Reed and Sam Baldwin in Sleepless in Seattle. When Baldwin’s son, Jonah (Ross Malonger), calls a radio station to find romance for his widower dad, recently engaged Reed tunes in to hear. There’s something about the story she can’t resist. Naturally, Reed travels across the country to stalk Baldwin and eventually leaves her fiancé to be with him.

While You Were Sleeping (1995)

Rom Coms
Image Credit: Hollywood Pictures and Caravan Pictures

Train ticket taker Lucy (Sandra Bullock) witnesses a man get mugged. Peter (Peter Gallagher) turns out to be the same man Lucy has a secret crush on. When Peter ends up in a coma, Lucy visits his hospital room, and his family mistakes her for his fiancé. Lucy plays along and winds up staying for Christmas (Ick). After all the lying and trickery, she winds up with his brother. Be still my heart!

My Best Friend’s Wedding (1997)

Rom Coms
Image Credit: TriStar Pictures

My Best Friend’s Wedding teaches the invaluable lesson that we always want what we can’t have. Julianne Potter’s (Julia Roberts) best friend, Michael O’Neal (Dermot Mulroney), is getting married. The two have known each other for years, but Potter only now realizes she loves him. Potter tries to get rid of Kimmy Wallace (Cameron Diaz), O’Neal’s fiancé, and steal him for herself. What a selfless friend.

You’ve Got Mail (1998)

Rom Coms
Image Credit: Warner Bros.

Tom Hanks (Castaway) stars alongside Meg Ryan (When Harry Met Sally) in a tale of two cheaters. Yes, you read that right. Kathleen Kelly (Ryan) can’t wait for her boyfriend, Frank Navasky (Greg Kinnear), to leave every day so she can get online. She doesn’t realize her online crush is business competitor Joe Fox (Hanks). Kelly and Fox eventually realize they’re perfect for each other. Who cares about their original partners, right?

Never Been Kissed (1999)

Rom Coms
Image Credit: 20th Century Studios

In this 21 Jump Street-esque rom-com, Drew Barrymore (Blended) is Josie Geller. Gellar is a 25-year-old reporter sent to spy on teenage children to help parents better understand their kids. If this isn’t inappropriate enough, the school’s English teacher falls for Geller, despite believing she’s a 17-year-old.

The Wedding Planner (2001)

Rom Coms
Image Credit: Columbia Pictures

Jennifer Lopez (The Cell) stars as wedding planner Mary Fiore in The Wedding Planner. After almost being run over by a dumpster, Fiore falls for doctor and savior Steve Edison (Matthew McConaughey). The catch? Edison is engaged to one of her clients. The two eventually wind up together. Who could resist a man who ditches his current fiancé for the wedding planner?

Failure to Launch (2006)

Rom Coms
Image Credit: Paramount Pictures

Is it me, or do a lot of rom-coms base protagonist relationships on lies? Failure to Launch stars Sarah Jessica Parker (Sex and the City) and Matthew McConaughey (Fools Gold) as Paula and Trip. Despite being 35, Trip still lives with his parents. Trip’s parents hire Paula to make their son fall in love with her so he’ll leave their house. Romance ensues. At least there wasn’t a disastrous sequel to sit through.

The 20 Best Romance Movies of All Time: Love Stories That Captivated Our Hearts

Pride and Prejudice Focus Features
Image Credit: Focus Features

Ready for a dose of romance? Check out our ultimate list of the 20 most unforgettable love stories ever told! As a self-proclaimed cinema enthusiast, I’ve watched countless heart-melting movies, and trust me; these films will stir up all the emotions within you. Whether you’re an old romantic or new to the world of love, this collection caters to every romantic soul. So, grab your popcorn, tissues, and prepare to fall head over heels for these iconic films.

The 20 Best Comedy Movies of All Time: Laugh Your Way Through the Ultimate List

The Truman Show Paramount
Image Credit: Paramount Pictures

Looking for a good laugh? Look no further! Our list of the top 20 comedy movies is here to brighten your day and leave you in stitches. This list will have you doubled over with laughter, from hilarious characters to unforgettable punchlines. Don’t miss out on the comedic gold waiting to be discovered. Click and prepare for a joyride through the best of the best in the world of comedy films.

The 20 Best Music Movies of All Time: Lights, Camera, Rock’ n’ Roll!

Bohemian Rhapsody 20th Century
Image Credit: 20th Century Fox

Get ready to be swept away by the mesmerizing blend of storytelling and music in our selection of the top 20 music movies ever made. From jazz beats to timeless rock anthems, these films deliver a symphony for your senses. Prepare to be moved, entertained, and immersed in the captivating world of music. Popcorn in hand, volume turned up, let the journey begin!