Ruby & Jeff go to New York City for Ruby's appearance on Rosie O'Donnell's radio show. They walk and Ruby struggles when she constantly is bumping into the passing people. Ruby appears on the radio show and tells Rosie about what she has been going through. She also meets at Rosie's house to discuss more, where she thinks Ruby has been sexually abused, something that Ruby denies. While in New York, Ruby & Jeff do more walking and Jeff records on the camera. The season concludes with Ruby talking with Jeff atop the arch bridge in New York.