Episode 69 of "Futurama"
s05e13 Bend Her

Bender faces his greatest challenge when he tricks his way into the 3004 Earth Olympian and wins several events, but he must endure the final and most revealing test to receive his medals. When Bender has a date with a major robot celebrity, Calculon, he sees this as an opportunity to be wined and dined like never before. When Bender realizes there's an inequity of feelings, he enlists Fry's and Leela's help to stage a "soap opera death".