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

A day in the life of a Chicago cab driver is examined as he picks up fares from the good and bad parts of the city and emotionally connects to many of his passengers.

Longtime friends Ronny and Nick are partners in an auto-design firm. They are hard at work on a presentation for a dream project that would really launch their company. Then Ronny spots Nick's wife out with another man, and in the process of investigating the possible affair, he learns that Nick has a few secrets of his own. As the presentation nears, Ronny agonizes over what might happen if the truth gets out.

Former top U.S. security adviser Elizabeth "Libby" Lamm is threatened by associates from her dark past including Rachel Burke a steely, commanding politician with an unwavering knack for achieving her goals. Colluding with Rachel is Adrian, an unyielding, patriotic chief of staff. Martin harbors another type of obsession with Libby in this story of betrayal and regret.