Chi Girl (1999)

This offbeat comedy about love and romance won writer director and actress Heidi Van Lier top honors a Grand Jury Prize at the 1999 Slamdance Film Festival Heather Green Van Lier is a journalist with an alternative newspaper in Chicago who is obsessed with her exboyfriend Randy Joe Kraemer is in turn obsessed with Heather A wouldbe documentary filmmaker Randy constantly films her sometimes without her knowledge When Heather takes up a challenge from Randy and announces she can seduce the next man she meets her desperation makes it clear shes had bad luck with men for a very good reason When Heather finally does meet the man of her dreams a goodlooking attorney named Cliff