Saturday Night Live Season 0, Episode 574 : SNL Digital Short: Seducing Women Through Chess

In an early '80s-style instructional video, a nerdy man dressed like Carl Sagan (Samberg) shows viewers how to seduce women by playing chess, but the first two women (played by Nasim Pedrad and Abby Elliott) beat him. The instructor then changes the game to checkers and still gets beaten by a woman (Kristen Wiig). He tries Jenga, but ends up knocking the tower over. He tries eating glass, but ends up scaring the woman he's trying to seduce (played by special guest Olivia Wilde). The instructor (with his lips and mouth now bandaged up) gives up and lectures on how to hire a prostitute. The prostitute (played by episode host Jason Segel) offers sex to him for $5000, but the instructor only has $60. The instructor is stabbed and robbed of his money. Before dying, the prostitute comes back and beats him at chess.

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