The Sweetest Thing Dec 17

Released in 2002

A girl finds she is forced to educate herself on the etiquette of wooing the opposite sex when she finally meets Mr. Right.

Starring
Cameron Diaz as Christina
Christina Applegate as Courtney
Selma Blair as Jane

Trivia:
The man in the leather coat  that picks-up Christina Applegate in the bar is her then-husband, Johnathon Schaech.

Rumour has it that the movie is based mainly on writer Nancy Pimental’s relationship with friend Kate Walsh.  Nancy make a cameo as the “vomit girl” in the club when Peter’s brother is inviting Christina back to the hotel for a party.