![]() as Randy Jensen & Jack Jericho respectively. There was also a 1987 film of the same name starring Molly Ringwald and Robert Downey Jr. The second season featured nine contestants with the second season winner being the 27 year old Simeon Moses. The winner of the first season was Alvaro "Kosmo" Orlando. ![]() As the show progresses 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". ![]() Each episode the men are given challenges that involved picking women up in different situations, such as: on a bridge during the day or in a nightclub. Throughout the show the contestants are tutored in the art of "pickup" as taught by Mystery and his wings. ![]() The first season featured eight male contestants that had previously been unsuccessful in love and relationships. ![]()
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