Chi Girl (1999)

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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 ex-boyfriend. Randy (Joe Kraemer) is in turn obsessed with Heather. A would-be 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 she's had bad luck with men for a very good reason. When Heather finally does meet the man of her dreams, a good-looking attorney named Cliff