Common Sense Note
Parents need to know that 10 Things I Hate About You has lots of references to sex, even by the standards of teen comedies, and especially a number of references to male genitalia, including a boy who draws a picture on the face of another and a boy who pretends to expose himself in the lunchroom, using a bratwurst, as well as the usual teen references to who has "done it." There is a wild party, with teen drinking and smoking, and brief references to drug use. The scene in which a girl bears her breasts to a teacher is worth discussing.
Many references to sex. Kat flashes her breasts at a teacher as a diversion (nothing shown). Kat and Bianca's dad is an obstetrician and makes his daughters wear a fake pregnant belly before they go on dates. Senior Kat discusses a bad sexual experience in 9th grade.
Drugs / Tobacco /
One teen character gives up smoking to attract a girl. Drinking at an out-of-control high school party. Main character throws up after drinking and dancing on a table.