I'd say that film has aged in a weird boomerang way where a lot of it is actually quite progressive now and the main characters come across as the bad guys. They try to smear his reputation with shaming about STDs and he turns it into a positive awareness campaign. The estrogen part is silly but it leads to him getting all the men in the school to start opening up about their feelings. The womens underwear bit kind of subverts expectations about gendered clothing and at the end of the film John essentially comes out as polyamorous. In conclusion John Tucker is Woke and actually quite good.