When filmmaker Tim Kirkman breaks up with his New York boyfriend, he heads back to his hometown in North Carolina to try to make sense of how his life has turned out. For some unclear reason, he attempts this task by first trying to make sense of U.S. Sen. Jesse Helms' continued political success. How can the (apparently) outwardly tolerant and friendly citizens of North Carolina regularly vote for Helms, who is widely regarded as one of the most racist, homophobic, and downright mean people in the U.S. Senate? Kirkman is more successful at sorting out his own feelings than he is at dissecting the often hypocritical and contrary nature of politics, let alone the appeal of one of the South's most enduring demagogues. Consequently, Dear Jesse is somewhat troubling: Kirkman may have problems with what Helms has to say, but is his public disdain any more fair and justified than Helms' statements? On the other hand, some found footage of gaybashing victim Matthew Shepard filmed at an anti-Helms rally illustrates the threat posed by outspoken opponents of civil rights. Personal attacks may be part of an effort to ultimately unseat him, but what are Helms' motives? In the film, the senator responds to a mother's letter describing the AIDS-related death of her son more or less with a cold "he got what he deserved," indicating that his motives may be as despicable as his opponents insist. Kirkman seems to be having fun finding himself by taking pot shots at Helms, and why not?