In truth, I haven't actually watched this in ages. However, I'll always remember liking it back upon its release in '99, making me an 11th-grader at the time. So the timing was pretty good when it popped up that year. It was perhaps the first example I remember of leaving the theater thinking about how I enjoyed it, while one friend I saw it with passed it off as an awkward "chick flick", bt didn't care what he thought of my opinion on it, which was quite positive.
The story here doesn't center on so much as revolve around bitter teenager Kat Stratford (Julia Styles). She's a bit of a loner, and not very-well liked due to her negative attitude towards basically everything. Her sister, Bianca (Larisa Oleynik), is the popular, pretty girl in school who everyone seems to desire. As a result, they have a pretty toxic sisterhood between them.
The sisters live with their overprotective father, Walter (Larry Miller), under the house rule that they are not to date until after they graduate high school. While Bianca is interested in dating, Kat doesn't really want anything to do with it, and therefore their father makes a deal with Bianca; she can date if Kat starts dating. Meanwhile, smitten-with-Bianca, is one Cameron James (Joseph Gordon-Levitt). New to the school, he's shown the ropes by the awkward and geeky Michael Eckman (David Krumholtz) and warned about not pursuing his interest in Bianca due to their father's rule.
As a result, Cameron works with Michael on devising a plan to get someone to date Kat so that he can have some sort of shot at dating Bianca. This plan involves bringing in tough guy, Patrick Verona (Heath Ledger) who Cameron believes would be about the only guy who would potentially put up with Kat's attitude. Anyway, the whole thing does become a pretty big mish-mash of love interest vs love interest, and can get a bit complex at times. I haven't even mentioned Bianca's interest in the cocky senior model, Joey Donner (Andrew Keegan), but I could be here all day explaining away.
For me, I suppose the charm of the film comes from the idea that the plot is so very "high school". It's also not so much about "getting laid" as it's about actually falling for someone and the desire to be with that person. It has its moments, but you can't very well look at this movie and say it's a raunchy, although it still feels very "teen movie". I'd put this one a little more alongside something like 'Can't Hardly Wait' than something like 'American Pie'. Being that it was '99, there's also that bit of a nostalgic factor. In the late 90s, teen movies really made a comeback, and I daresay this was one of the better of them.
As far as this being a recommendation, I suppose it's for those of us who can appreciate something a little more "Hughes-esque" when it comes to a teen movie execution. It's for 'Breakfast Club' or 'Pretty in Pink' fans a touch more than it's for 'American Pie' or 'Superbad' fans. All that said, I'm fairly bias towards teen movies, myself. I really do enjoy a good coming-of-age movie, and this is quite a good one. If nothing else, it's fun to go back on, recognizing some of those forgotten faces, seeing Heath Ledger's breakthrough performance and seeing where we dropped Joseph Gordon-Levitt off as a young up-and-comer, before picking him up again in '500 Days of Summer' as an a sudden fan-favorite (although for me, that was 'Inception').