In The Curious Case of Dean Winchester, the boys (including Bobby) face a man-witch capable of adding or taking years off a man's life with a simple round of Texas Hold-Em. Dean learns that he needs to take better care of himself, in order to survive old age. Sam proves that wisdom and wit can be found in the young. And Bobby finds himself on the other end of a lecture on self-worth, because it's not Halloween unless you learn a lesson.

Supernatural Season 5, Episode 7. Air Date: October 29, 2009

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