I've somehow gone through life without ever seeing this "classic", despite knowing most of the references second-hand 😄 Some parts were therefore a bit weird, almost deja vu like, but I was actually surprised how well the movie holds up. There's the occasional extremely dated bit of slang and the fashion is definitely of its era, but neither ever jumped me wholly out of the film. The cast is brilliant and performances were all-around great, plus the humour still landed a lot of the jokes. It also doesn't suffer from much overly-insensitive, edgy comedy like a lot of late '90s films, nor does it hyper-sexualise the female leads (another prevalent trope for that time period), likely due to actually being written and directed by women.
My one main niggle throughout was "Africa". I think the movie just about swerved the potential for racist tropes here (narrowly, admittedly, at times), but it still plays strongly into American ignorance about the continent in general. For starters, a character that has grown up living "on the savannah" (which feels problematic in its own right) probably wouldn't refer to her previous home as just "Africa", nor would she just walk up to the black kids and say "hey" in an arbitrary African dialect (even putting aside the fact that she's clearly more intelligent than that anyway). She'd understand that the (again) continent of Africa contains a multitude of countries, languages, cultures, and peoples. As I say, it's ignorant, not racist, but it still felt a bit cringy.
The result is a fun movie with a solid core that stands the test of time. There's nothing too deep going on here, it's still a deeply American high-school setting with elements of rom-com, but there's also very little to complain about.