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This installment of Supernatural is titled "The Curious Case Of Dean Winchester." During the episode, Bobby risks his life by gambling 25 years of his life on a poker game, which is run by a witch. That can be risky.

From there, Dean tries to save Bobby, but winds up drastically aging.

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Supernatural Season 5 Episode 7 Quotes

Sam: It's like Grumpy Old Men.
Dean and Bobby: Shut up, Sam!

Sam: Have you seen you? You look like...
Dean: ... the old chick in Titantic. Shut up.