The Pickup Artist is an American reality television dating themed game show that aired on VH1. The show was hosted by pickup artist Mystery and his wings J-Dog and James Matador, with Tara Ferguson replacing J-Dog in season 2. The first season featured eight male contestants that had previously been unsuccessful in love and relationships. Throughout the show the contestants are tutored in the art of the "pickup" as taught by Mystery and his wings. In each episode the men were given challenges that involved picking women up in different situations, such as on a bridge during the day or in a nightclub. As the show progressed the men were instructed to pick up women of varying levels of difficulty, such as in the second to last challenge of the first season where the men had to pick up a stripper, described by Mystery as "the ultimate challenge." The winner of the first season was Alvaro "Kosmo" Orlando. The second season featured nine contestants and aired in October 2008, with the second season's winner being 27-year-old Simeon Moses.