Unless you had a really cool Regina George-esque mum, an older sister to spy on or great sex ed (and most of us didn't, let's be honest), you learned about love and relationships like the rest of us – from the great, glossy, OTT, saccharine, angsty rom-coms of the '90s. And unsurprisingly – although at the time we were shook to the core – our awkward experiences of love and sex were never quite as monumental, beautiful and impeccably lit as they were in the movies. That's probably a good thing because in retrospect, these movies gave us some strange, strange advice.
10 Things I Hate About You
Forgiveness is important. It's essential to happiness to overlook some things in the great name of love. But it's probably not as important as 10 Things makes it seem. In real life, if your boyfriend forgets your birthday or shows up late to a date or, I dunno, gets to know you intimately because he's being paid to do so as part of a convoluted bet, you probably shouldn't let him off just because he gives you a mint-green Fender Strat.
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Never Been Kissed
Being a teenager, especially if you're not a cool, fit one, can be really brutal. Boys will scoff at your Day Glo outfits and literary ambitions and call you Josie Grossie and play cruel, horrible jokes on you, but that doesn't mean you won't be successful in 'real life'. And even if you’re not satisfied with that ‘real world’ life once you reach your 20s, despite what Never Been Kissed might pretend, reliving it all by hanging out with teenagers won’t make you cooler. It isn’t healing, it’s just… kind of creepy. Admittedly though, every time I rewatch Never Been Kissed I still learn the same lessons about love and life that I did at 14: that no matter how old you are, getting revenge and redemption as a former nerd feels bloody good.
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Clueless
Glossing over the bizarre familial relationship between Cher and ageless adonis Paul Rudd, Clueless is the first of many '90s rom-coms which instil in us the incorrect notion that being a virgin in your group of friends at the ripe old age of 16 is worthy of derision and a light existential crisis. Later you learn, of course, that not only is it pretty standard to be a sexually frigid 16-year-old but also that the idea of virginity is a harmful social construct. It takes you a long time, though, to realise that it's ridiculous to imagine that nothing in your life – whether you're a sad, old teacher or you live in a rose-tinted teenage fantasy of great grades, wealth, friends and family – will be complete until you get yourself a boyfriend.
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She's All That
Following in the great Clueless tradition of 'a boyfriend will fix everything and make you happy', She's All That teaches us timeless incorrect lessons, the most ridiculous being that you're nothing without a makeover (even if that makeover is losing two inches of hair and putting in contact lenses). And just like 10 Things I Hate About You, it teaches us to go back to hot guys who may have only gone out with us because of a convoluted laddish bet (it's weird that so many '90s films have the it-was-a-bet premise). She's All That is the most iconic example of the harmful, archaic 'hot without glasses' cinematic trope, and although it's one of my favourite films of all time, as a bespectacled 13-year-old it wasn't much fun to watch.
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Drive Me Crazy
Subcultures are important, but they never seem as concrete and monumental as they do in films like Drive Me Crazy, where Melissa Joan Hart and beautifully tousled Adrian Grenier are kept apart by social groups of jocks and weirdos that never really translated to boring, grey British secondary schools. But the main thing Drive Me Crazy told us, like so many other films, was that until you're 'made over' (even with something as simple as a new tailored jacket-jumper combo and a fleeting interest in popular sports), you're not interesting or accessible enough to be attractive or loved.
It's pretty maddening how pervasive the makeover trope is in '90s teen movies, especially realising that, as a teenager, it wasn't even a trend I noticed. It was just something I, like so many other insecure teen girls, took as fact: that you have to look good to be lovable.
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American Pie
I was never allowed to watch American Pie. Watching a sweaty teenage boy penetrate an apple pie was where my mum drew the line. And the fact it was forbidden made me think it was gonna be the worst of the worst, the most ridiculous of teen sex and relationship set-ups when I watched it as an adult. But aside from the pervasive myth that virginity is important, it's one of the most realistic films there is about early sexuality. Losing your virginity and navigating your first 'proper' relationship as a teenager is not always a magical journey. Really, everyone is as sweaty, uncomfortable and clueless as the American Pie boys. The film really is ahead of its time in (some) of its views, not only towards relationships but towards teenage sexuality.
Hidden among all the squicky humour it includes a young Natasha Lyonne casually discussing female masturbation, a group of boys talking about the importance of "legitimate, consensual sex" and buying condoms, a parental lecture on the importance of the clitoris, and a girl who will major in post-feminist theory telling a guy how to speak to women respectfully. Ostensibly it's a gross, cheesy movie about sex, but the subtext is that learning what the person you care about enjoys matters much more than telling all your mates you lost it.
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Varsity Blues
As well as being one of the most iconic, often parodied '90s scenes of all time, Ali Larter wearing a whipped-cream bikini actually passes on a valuable lesson: You shouldn't follow men to greatness, you need to do it for yourself. Darcy Sears might have started off thinking she could follow talented football player boyfriends out of her boring AF small town, but the probably life-changing experience of being rejected while wearing only whipped cream made her realise she could get out and enjoy her own life herself. Thankfully, the rest of us were imbued with the message without having to experience the whipped-cream rejection ourselves.
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Cruel Intentions
Despite the impressive soundtrack and Craft -esque impeccable fashion, Cruel Intentions introduces you to an uncomfortable idea as a teenage girl. There are good girls – the virginal, earnest, kind Reese Witherspoons of the world – and bad girls – the scheming, unsatisfied, manipulative Sarah Michelle Gellars of the world, and you should always be the good girl.
Otherwise you'll end up alone, unhappy and with your sins exposed while "Bittersweet Symphony" plays ominously in the background.
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