For a time, Barry dated public-radio personality Ira Glass. She briefly joined him in Washington, D.C., but a few months later, in the summer of 1989, she moved to Chicago to be near fellow cartoonists. Glass followed her there. Reflecting on the relationship, she called it the "worst thing I ever did," and said he told her she "was boring and shallow, and...wasn't enough in the moment for him." She later drew a comic based on their relationship titled "Head Lice and My Worst Boyfriend", which was later included in her book "One! Hundred! Demons!..." Glass has not denied her assertions, and told the "Chicago Reader", "I was an idiot. I was in the wrong...About so many things with her. Anything bad she says about me I can confirm."