Kent (Kent Osborne) is a single, 40 year-old cartoonist who lives alone with his fluffy and sometimes finicky cat in Los Angeles. He spends most of his work days sketching cartoons alongside his friend, Kev (Kevin Bewersdorf), and most of his non-working hours taking hits from his bong and chatting with people on Chatroulette. A cute environmental journalist named Kate (Jennifer Prediger), one of Kent's Chatroulette acquaintances, crashes at Kent's house for the weekend. Kent is well aware that Kate is currently in a long-term relationship, but he is unabashedly attracted to her intelligence, sense of humor, flirtatiousness and openness nonetheless. It does not help Kent's state-of-mind that his time spent with Kate grows increasingly sexually charged: conversing frankly about masturbation and homoerotic fantasies, posing for raunchy photos and picking up an attractive bi-curious woman (Josephine Decker) on Craigslist. Kent is receiving mixed signals from Kate and it is really screwing with his head.