1999's 'Cruel Intentions' is an ambitious movie which just about manages to be less than the sum of its part. The film was intended as a vessel for Sarah Michelle Gellar, who was at the peak of her 'Buffy the Vampire Slayer' fame. It's based on an 18th-century French novel titled 'Les Liaisons Dangereuses,' but re-imagines all the characters as wealthy, bratty American high-schoolers.
As a consequence of that, Joshua Jackson's character Blaine Tuttle becomes a throwaway stereotype; he's a token gay character who's used firstly to be catty, and then secondly to seduce and entrap a straight-but-questioning character with the intention of blackmailing him. As Jackson's is the only truly gay character in the film, it's not a flattering portrayal of the community. The general critical consensus of the movie is that it means well, and it tries hard, but too much of the text's heart has been lost by changing the period and location.