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In The Pick-Up Artist 2, nine misfits will live together, learn together and love together as they compete for the title of "Master Pick-Up Artist.". The second season featured nine contestants and aired in October 2008, with the second season's winner being 27-year-old Simeon Moses. The Pickup Artist - watch You are able to buy "The Pickup Artist - Season 2" on Apple iTunes, Amazon Video as download. People who liked The pick-up artist season 2 also liked. The Pick-up Artist Season 2 Episodes. 2007-2008; 2 Seasons; VH1; Reality; TVPG. Watchlist. Where to Watch. An expert at picking up women shares his In Season 2 of The Pick-Up Artist, nine misfits will live together, learn together, and love together as they compete for the title of Master Pick-Up Artist It's off to Phoenix for season 2 as Mystery is joined by Matador and Tara. the contestants first challenge is to be observed as they approach women inside aThe second season featured nine contestants and aired in October 2008, with the second season's winner being 27-year-old Simeon Moses.