Life Lessons We All Learned From Romantic Comedies In 1999

I can’t tell if I loved romantic comedies in the 90s because I wasn’t hopelessly jaded yet, or because they were just better back then. It seems like every teen rom-com today is a re-make of a re-make, and we all know the only sequel worth watching is Zenon: The Zequel. While some people might have learned about life from from Disney fairy tales, 1999 romantic comedies were my drug of choice. They were all my pre-tween self needed to create false expectations for life, love, and the eventual appearance of a sexy step-brother to sweep me off my feet. Everything I know about life I learned from people in their mid-20s masquerading as teenagers in the 90s.

She’s All That (1999)


She’s All That taught me that once anyone takes their glasses off, they’re automatically a smokeshow. Even as a tween, it shocked me that anyone would think Rachel Leigh Cook was an ugly beast just because she was rocking a ponytail.


Pro tip for the ladies, if you’re looking to land a man who loves you so much he’d go naked for you in public, just pop some contacts in and unhook your hair elastic.


In movies, the main character always glamorously descends the stairwell, seemingly in slow motion. In real life, if you did that your date would wonder why you were drunkenly hobbling down your rickety apartment stairs, but it’s the thought that counts.


The most important lesson of the movie? Embrace your success while you have it. Back in ’99 we all assumed Freddie Prinze, Jr. was the next Brad Pitt, only better looking. Now he’s basically a stay-at-home Dad, I assume, because we haven’t heard from him in ages. He may be married to Buffy, but he’s not exactly killing it in the Hollywood department. Another worthwhile lesson? The importance of anti-aging creams (or botox), starting at a young age. It may be a hundred years later, but Freddie looks like Benjamin Button, only better.

10 Things I Hate About You (1999)


This movie mostly taught me the definition of “pensive.” It also taught a decade of underage kids the importance of black panties. After all, “You don’t buy black lingerie unless you want someone to see it.” This secretly raunchy rom-com brought us the classic line, “What is it with this chick? She got beer flavored nipples?” which I can’t help but think about whenever guys are going crazy over someone, to this day.


More importantly, its best lesson was that whenever you had to read Shakespeare for school, there was always a contemporary movie that was far more entertaining.


Sometimes I wonder if you can ever just be whelmed, because that’s how I feel about rom-coms today in comparison to this goldmine. It had a sassy, sarcastic, feminist heroine, a bad boy turned good, and ska band Save Ferris. Now that’s 90s perfection. There was recently a failed 10 Things sit-com, proving that you can’t recreate the magic. Especially without Heath Ledger (RIP).

Drive Me Crazy (1999)


Like Clueless, and later Gossip Girl, Drive Me Crazy taught the world that it’s okay to fall for your step-brother (but only if he’s really cute). Otherwise it’s just too Deliverance-y for words.


Drive Me Crazy taught tweens nationwide that the best way to make anyone jealous is with someone new, especially if you get him a makeover and force him to ditch his hideous turtleneck and alterna-girlfriend. More importantly, he has to have the star power of someone bound to be a bona-fide celebrity. You can’t exactly make someone jealous with a Turtle, now, can you? Apparently, Elijah Wood was supposed to star opposite Melissa Joan Hart but he looked too young. Just imagine Elijah Wood as Vinny Chase for a minute, and you’ll be glad that Adrian Grenier exists.

Never Been Kissed (1999)


Before The 40-Year Old Virgin, there was Never Been Kissed. It’s funny to imagine a world where Drew Barrymore is eternally pure, but this movie made it happen.


Josie Grossy, as a character, was a serious spoiler alert that high school might not be the best four years of your life if you were on the socially awkward side of things. Luckily, it also shows that people who peak in high school don’t exactly have a bright future in front of them (see also: Romy and Michelle’s High School Reunion).


Fortunately, I peaked in college, instead. While it might all be downhill from here, at least I learned these valuable lessons early in life. While I’d like to think I didn’t peak in 1999, I can’t help but wonder if romantic comedies did.

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Margaret Abrams

Nothing Margaret writes should be taken seriously by anyone, including her parents, employers, or gentleman callers. She's currently coping with a quarterlife crisis.

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