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Crowley also makes it possible for Bobby to walk again.

While possessed by a creature she created, he kills his old friend Rufus Turner.Sam visits Bobby on his release from Lucifer's Cage, and Bobby agrees to keep Sam's return a secret from Dean, who Bobby sees at having a chance at a normal life.Following his reunion with Sam, Dean (worried because of Sam's cold and relentless behavior) calls on Bobby for support.Bobby, though he feels himself rusty, helps and is punished in an unknown manner for it, though he leaves Sam a note in which he states that it was worth it.Since the death of his wife Karen Singer, the only other romantic interests in Bobby's life that we've met are Eleanor Visyak and Annie Hawkins.

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Bobby's reputation around Sioux Falls is that of a troublesome old drunk, but following his role in quashing a zombie uprising, the local sheriff, Jody Mills, comes to develop a friendship with him, that appears to have the potential to become romantic; with one kiss is exchanged prior to his death.

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