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A man and woman dance on a dance floor in this image from Revolution Studios.
Gen Z will never be the same after watching the “Thriller” dance in “13 Going on 30.” (Image: Revolution Studios)

Streaming services churn out so much material so quickly these days that most movies come off as kitschy and cliché. I always cave and watch what’s new, but most of the time, it leaves me wishing for the days of quality films. Today, I couldn’t quote a good one-liner or tell you which scene I think a movie will be remembered for. 

That’s not to say I don’t enjoy newer Gen Z movies, because I’ve seen a few that I did — like “To All the Boys I’ve Loved Before.” However, the golden age of rom-coms has passed us by, and the younger generations need to see these prime examples of what rom-coms were back then.

Whether you want to take a trip down memory lane with me or see what we “old folks” watched on girls’ night, you’re in the right place. The movies on this list are all iconic for one reason or another and picked to represent rom-coms of their era.

The ’80s

‘The Princess Bride’ (1987)

A couple stands in the doorway of a barn looking out into rolling hills in this image from Buttercup Films Ltd.
Love always finds a way … except for the man with six fingers on his right hand in “The Princess Bride.” (Image: Buttercup Films Ltd.)

“The Princess Bride” is a rom-com classic from the ’80s, and I’ve yet to meet someone who didn’t enjoy it. The story is full of adventure, action, romance, and comedy, leading to many iconic characters and lines. Regardless of how unrealistic the large rodents were (this was before the age of CGI), I was still terrified of them. Farmer boy Westley (Cary Elwes) sets off to save his love, Buttercup (Robin Wright), when she’s whisked away to marry the dreaded Prince Humperdinck (Chris Sarandon). 

“The Princess Bride” is still my go-to movie whenever I have a cold. Check it out on Disney Plus.

The ’90s

‘Pretty Woman’ (1990)

A scantily dressed woman lies on the floor with a bottle of Champagne in this image from Touchstone Pictures.
“Pretty Woman” is largely considered one of Julia Roberts’ breakout roles. (Image: Touchstone Pictures)

Admittedly, I’m not a Julia Roberts fan. However, her portrayal of Vivian Ward was exceptional, and I can see why it took her career to the next level. “Pretty Woman” follows a hooker in L.A. when she’s hired for a week by a businessman (Richard Gere) to be his date to social engagements — no hanky-panky required. In her free time, he rains money on her to take herself shopping and live the lifestyle she would have if they were truly involved. Then comes the question: Will Vivian return to days on the streets when the week is over?

“Pretty Woman” is a captivating rom-com with an iconic ending that Gen Z should see for themselves — and it’s available on Hulu.

‘Clueless’ (1995)

Three teenage girls holding books and binders walk in a sunny school courtyard in this image from Paramount Pictures.
“Clueless” is an entertaining take on Jane Austen’s novel “Emma.” (Image: Paramount Pictures)

On the surface, “Clueless” is just a silly, fun story. Sure, my girlfriends and I watch it for the outfits and giggle where we’re supposed to, but we also notice the social aspects director Amy Heckerling captured so well. It’s ultimately a commentary on a woman’s supposed role in society and how divided the social classes are. But that doesn’t mean we can’t enjoy it simply because there’s a young Paul Rudd in it. 

Watch “Clueless” on Paramount Plus

‘Ever After: A Cinderella Story’ (1998)

A man gazes up at a woman dressed as an angel in this image from Fox Family Films.
The best Cinderella story requires a girl ready to change her life — and maybe a prince. (Image: Fox Family Films)

“Ever After” is another favorite of mine; it was constantly in my rotation of VHS tapes growing up, and I’m amazed that it never wore out no matter how many times I watched and rewound it. It’s a beautiful take on the Grimms’ fairy tale, “Cinderella.” The opening scene shows Grande Dame (Jeanne Moreau) telling the Brothers Grimm of her ancestor: the original cinder girl. Danielle (Drew Barrymore) is treated like a slave by her stepsisters and stepmother, but she doesn’t let this wear her down. She takes matters into her own hands instead of waiting for Prince Henry (Dougray Scott) to rescue her. 

You’ve probably seen more recent versions of “Cinderella,” but even Barrymore says this is her favorite film from her career. Watch “Ever After: A Cinderella Story” on Disney Plus to see why.

‘10 Things I Hate About You’ (1999)

A young couple with paint streaks in their hair sits in a park in this image from Touchstone Pictures.
This rom-com starring the late Heath Ledger and Julia Stiles is a modern spin on a Shakespearean play. (Image: Touchstone Pictures)

“10 Things I Hate About You” is among the best teen rom-coms. It’s loosely based on William Shakespeare’s “Taming of the Shrew.” New boy Cameron (Joseph Gordon-Levitt) desperately wants to date pretty, popular girl Bianca (Larisa Oleynik). However, Bianca is only allowed to date if her older sister Kat (Julia Stiles) does, and that’s highly unlikely since she’s antisocial. So Cameron pays bad boy Patrick (Heath Ledger) to woo her and convince Kat to date him. It’s a fun ride with quite the ensemble cast and one tear-inducing monologue. Gen Zers may have even come across that classic scene on TikTok.

Watch “10 Things I Hate About You” on Disney Plus.

‘She’s All That’ (1999)

A teenage girl and boy stand on the beach in this image from Tapestry Films.
Anybody can be somebody with enough effort, as Laney (Rachael Leigh Cook) learns. (Image: Tapestry Films)

“She’s All That” is a classic glow-up story. Recently dumped, Zach (Freddie Prinze Jr.) bets with his buddy Dean (Paul Walker) that he can turn anyone into the next prom queen. Dean picks out “unattractive” Laney (Rachael Leigh Cook) as their mark. Of course, as time passes and the transformation from nerdy to prom queen takes place, Zach falls for Laney. Honestly, Laney was never unattractive, and Zach should’ve seen that from the start. Even if the storyline is a bit basic, the ’90s outfits — many of which are totally back in style — are worth the watch.

Join me in watching “She’s All That” on Paramount Plus.

The Early 2000s

‘Legally Blonde’ (2001)

A woman dressed in all pink stands in a courtroom with a full audience in this image from Metro-Goldwyn-Meyer.
Never underestimate a woman on a mission — even if she’s dressed in all pink! (Image: Metro-Goldwyn-Meyer)

“Legally Blonde” is a movie that took a promising career start for the petite and lovable Reese Witherspoon to new heights. Witherspoon’s Elle Woods is a sorority queen with the cutest boyfriend (Matthew Warner) — until he breaks up with her. To get him back, she follows him to Harvard Law School. However, she soon finds that she’s more than capable on her own and has a passion for law. Elle is the epitome of never judging a book by its cover. 

With the third installment in the Legally Blonde franchise in the works, you’ll want to make it a double feature at your next girls’ night. “Legally Blonde” and its sequel, “Legally Blonde 2: Red, White & Blonde,” are streaming on Max

‘The Princess Diaries’ (2001)

A man in a suit and a woman in a white and gold ball gown talk in a dark garden by a fountain in this image from Walt Disney Pictures.
Every girl’s dream is to grow up and be a princess … except for this girl. (Image: Walt Disney Pictures)

“The Princess Diaries” is the ultimate glow-up rom-com — and true bibliophiles know it’s based on a book series. Mia Thermopolis (Anne Hathaway) is an average 16-year-old living in San Francisco with her single mother. But her life changes forever when the grandmother she’s never met shows up with stunning news: Mia is the heir apparent to the throne of Genovia, her grandmother being the current queen and ruler. Queen Clarisse (Julie Andrews) takes it upon herself to prepare Mia for the throne. 

“The Princess Diaries” and its sequel, “The Princess Diaries 2: Royal Engagement,” are available on Disney Plus. This is definitely a Gen-Z must-watch, as it’s rumored a third installment may go into production.   

‘How to Lose a Guy in 10 Days’ (2003)

A couple laughs together outside while playing cards in this image from Paramount Pictures.
One lesson from “How to Lose a Guy in 10 Days?” Never make a bet unless you know you’ll come out on top. (Image: Paramount Pictures)

Honestly, I almost didn’t include “How to Lose a Guy in 10 Days” on this list, as it’s a pretty formulaic rom-com. However, Matthew McConaughey and Kate Hudson had fantastic chemistry, bringing us some conic scenes. Ben (McConaughey) bets he can make a woman fall in love with him in 10 days. Meanwhile, journalist Andie (Hudson) takes on an article about losing a guy in 10 days. Of course, these two meet, and thus romantic-comedic chaos ensues. Gen Z definitely needs to see McConaughey in his prime before the “McConaissance” of the 2010s.

“How to Lose a Guy in 10 Days” is streaming on Pluto TV. 

‘50 First Dates’ (2004)

A couple sits in a booth at a diner with a plate of waffles stacked to look like a house in this image from Happy Madison Productions.
Imagine having to win someone over every single day for the rest of your life. That’s the premise of “50 First Dates.” (Image: Happy Madison Productions)

“50 First Dates” is a fun movie. I appreciate that the leading man isn’t your typical dreamboat guy usually seen in rom-coms. Henry (Adam Sandler) thinks he’s found the girl of his dreams in Lucy (Barrymore). After spending an incredible day together, however, he’s confused when she doesn’t recognize him the next day. He learns that Lucy suffers from short-term memory loss and is unable to remember one day to the next. Henry decides this unusual issue doesn’t outweigh his love for her and sets out to win her over every single day. 

My favorite thing about this movie is that it was inspired by a true story. Watch “50 First Dates” on Amazon Prime Video

‘A Cinderella Story’ (2004)

A girl in a pink apron serves a boy her age from behind a bar in a diner in this image from Dylan Sellers Productions.
“A Cinderella Story” is about not letting your circumstances define you. (Image: Dylan Sellers Productions)

In the early aughts, many variations of “Cinderella” were aimed at the teenage girl market. Yet I’d argue that one of them, “A Cinderella Story,” was enjoyable for all ages. Sam (Hilary Duff) is a high school senior who has worked hard to gain admittance to Princeton. Her stepmother, Fiona (Jennifer Coolidge), is less than enthusiastic about losing the free labor Sam provides and deceives her by faking a denial letter from the elite college. 

“A Cinderella Story” is still a favorite of mine and perfect to rent on Amazon Prime Video when you want to watch heartthrob Chad Michael Murray in something besides “One Tree Hill.”   

‘13 Going on 30’ (2004)

A couple cuddles on a couch outside in this image from Revolution Studios.
Getting through your teenage years would be easier if you could see how your life would turn out and make changes to benefit your future. (Image: Revolution Studios)

Full transparency: I hadn’t seen “13 Going on 30” until it came to Netflix at the beginning of 2024. I’d always wanted to see it, as I love Jennifer Garner. I was far from disappointed. The movie was a delight and skyrocketed to the top of my list of favorite rom-coms. On her 13th birthday, Jenna (Garner) wishes she was 30, flirty, and thriving. She soon learns that every wish comes at a cost, and in this instance, it’s just too great of a price. 

For the most epic “Thriller” dance scene and much more, watch “13 Going on 30” on Netflix

‘Along Came Polly’ (2004)

A woman laughs and reacts to the man across the table from her in a restaurant in this image from Jersey Films.
“Along Came Polly” shows that the best things happen when you least expect them. (Image: Jersey Films)

As an avid “Friends” fan, Jennifer Aniston holds a special place in my heart, so naturally, I’ll watch any movie she’s in. Her portrayal of the eccentric Polly in “Along Came Polly” proves that Aniston is a true artist. She runs into an old friend from high school, Reuben (Ben Stiller), who has recently been dumped on his honeymoon. The two struggle to strike up a relationship with their polar opposite lifestyles. If you’ve ever suffered through a spicy meal when you can’t handle spice, then you know what I mean! 

“Along Came Polly” is streaming on Peacock. 

‘The Devil Wears Prada’ (2006)

A woman in an ill-fitting blue sweater stands with a notepad and pen in this image from Fox 2000 Pictures.
Many people have to learn the hard way what they’re willing to put up with for a paycheck, as Andy (Anne Hathaway) does in “The Devil Wears Prada.” (Image: Fox 2000 Pictures)

If I had to choose one movie that defined the aughts, it would be “The Devil Wears Prada.” It featured an incredible glow-up, career-defining roles, and a catchy soundtrack. It's all based on a novel of the same name, a fictionalized version of one woman’s real-life experience in the fashion magazine world. Andy (Anne Hathaway) takes on an assistant role for fashion magazine editor-in-chief Miranda (Meryl Streep), much to another assistant’s chagrin. Will Andy keep the job and the guy?

“The Devil Wears Prada” is so iconic that even my fiance enjoys watching it. Stream it on Max for your next movie night. 

‘Because I Said So’ (2007)

A mother and adult daughter cuddle in PJs on a couch in this image from Gold Circle Films.
There’s nothing quite as special as a mother-daughter relationship, which is exactly what “Because I Said So” showcases. (Image: Gold Circle Films)

“Because I Said So” is an underrated movie. It has a fantastic cast, including Mandy Moore, Diane Keaton, and Gabriel Macht. While I love a good rom-com for its romantic relationships, I also love this one for the mother-daughter relationship. Daphne (Keaton) is an overly-involved mother who interferes in the love life of her daughter Milly (Moore). It’s the ultimate feel-good movie where everything works out how it should. 

“Because I Said So” is available on Hulu.   

‘He’s Just Not That Into You’ (2009)

A man standing behind a bar converses with a woman seated at the bar in this image from New Line Cinema.
Women make too many excuses for men’s bad behavior. Case in point: “He’s Just Not That Into You.” (Image: New Line Cinema)

“He’s Just Not That Into You” has an ensemble cast (including Aniston) with intricately woven characters. Needy Gigi (Ginnifer Goodwin) isn’t great at reading the signs men give her, but when she meets Alex (Justin Long), he clues her into the secrets of dating. She finds Alex to be an untapped and willing source of dating advice and calls on him with all her problems. Dating today may differ entirely for Gen Z, but this film hits on some universal truths.

“He’s Just Not That Into You” is available to rent on Amazon Prime Video.   

Honorable Mentions

“While You Were Sleeping” (1995)

“There’s Something About Mary” (1998)

“You’ve Got Mail” (1998)

“Never Been Kissed” (1999)

“Sweet Home Alabama” (2002)

“Mean Girls” (2004)

“Confessions of a Teenage Drama Queen” (2004)

“Just Like Heaven” (2005)

“Catch and Release” (2006)

“John Tucker Must Die” (2006)

“The Holiday” (2006)

“Music and Lyrics” (2007)

“27 Dresses” (2008)

“Forgetting Sarah Marshall” (2008)

“Beauty and the Briefcase” (2010)

“Letters to Juliet” (2010)

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