1999 was THE year for teen movies: American Pie, She’s All That, 10 Things I Hate About You, Cruel Intentions, Varsity Blues, Jawbreaker and Dick were just a few of the releases. Now, they are all celebrating their 15th anniversaries. We’ve gone back to pick some of our favorite teen duos from the era. Trust us, it wasn’t easy.

“Goodbye, England’s Rose,” sang Elton John at the funeral of Diana, Princess of Wales, while the world watched with tears and empathy. On August 31, 1997, we lost the People’s Princess in a tragic, paparazzi-fueled car chase through the streets of Paris. Fate has taken a number of other much-missed public figures before their time; now we’re celebrating the life of England’s Rose and 12 other celebrities lost to tragedy.

Sometimes Cupid has a sick sense of humor. Or maybe he’s just bored. Judging from the random celebrity hookups and romances, it is hard to tell the difference. One thing is for certain: Beauty truly is in the eye of the beholder when it comes to these romances.

We loved her as Jen, the intriguing new girl with the troubled past on Dawson’s Creek. And we fell in love with her all over again as she blossomed in movies like Dick and then more grown-up fare like Brokeback Mountain. And she’s taken on one of the great American icons in My Week with Marilyn. What’s not to love?