This romantic comedy was released in 1999 and was directed by Gil Junger.

We are introduced to Cameron James (Joseph Gordon-Levitt) who is new to Padua High School and the first girl he sees is the beautiful Bianca Stratford (Larisa Oleynik) and falls in love.  Bianca’s father (Larry Miller) is very strict and it is common knowledge that she is not allowed to date.  Cameron decides that he will find a way to date her no matter what.  Bianca is interested in the very popular Joey Donner (Andrew Keegan).  Cameron and his friend Michael (David Krumholtz) devise a plan so that Cameron can date Bianca.

The Plan Unfolds

Bianca’s father will only allow her to date if her older sister Kat Stratford (Julia Stiles) also dates.  This is however a problem as Kat is not interested in dating and is known to be different and not interested in the social scene at all.  They realise that it is going to take a certain type of guy to date her.  Together with Joey, Cameron and Michael decide on Patrick Verona (Heath Ledger) who has a reputation for being a rebel and Joey makes a deal with Patrick.  If Patrick can get Kat to go out with him he will give him cash, which we suppose he otherwise could have tried to win by enjoying a bit of horse racing betting.  Patrick accepts the challenge and takes the money.

Patrick realises that is not going to be that easy to get Kat to go out with him and asks Joey for more money that Joey gives him.   After much persuasion from Patrick and Bianca who begs her to go to a party, Kat agrees.  At the party Bianca realises that Joey is actually very shallow and only talks about himself.  Meanwhile Kat gets drunk and becomes the life of the party.  We get the feeling that there is much more to Kat’s antisocial behaviour than meets the eye.

A Prom Conundrum

Patrick takes Kat home where she tries to kiss him, but he pulls away leaving Kat confused and very angry.  Bianca realises that Joey is not the guy for her and asks Cameron to take her home.  Bianca kisses Cameron.  Joey refuses to be defeated and decides to ask Bianca to the prom.  Bianca can only go to the prom if Kat also goes and he gives Patrick more money to get Kat to go to the prom with him.  Kat is angry with Patrick and refuses to go to the prom.

Bianca and Kat have a heart to heart where she shares with Bianca that she and Joey had been an item who had just used her and she did not want the same thing to happen to Bianca.  Kat decides to go to the prom with Patrick.  Bianca decides to go with Cameron to the prom.  Everyone is having a great time until Kat finds out that Patrick was only interested in her for the money.  She is furious and leaves the prom.

You will all have to watch this great film to find out if Patrick and Kat reconcile.