The Plot: In Season 7 Episode 20 "The Girl with the Dungeons and Dragons Tattoo", Sam and Dean become worried that since Bobby has died that he is turning into a vengeful spirit after Bobby attacks Dick Roman. Sam and Dean make the claim that over time that ghosts always turn into vengeful spirits. As the season concludes, at one point Bobby nearly chokes Sam to death. In the season finale, Bobby agrees to let Sam and Dean destroy the flask that his spirit was attached to thus sending him to the "other side".
Why it doesn't make sense: Sam and Dean are worried that they'll have to stop Bobby because he is turning into a vengeful spirit because they claim that ghosts ALWAYS turn into vengeful spirits, but I can cite at least two examples in the series where spirits had been dead for decades... even centuries and didn't turn vengeful. Humorously, just one episode prior in Season 7 Episode 19, Sam and Dean find themselves in an abandoned house full of ghosts. One of the ghosts was an 19th Century prostitute named Victoria who actually helped Sam and Dean in their quest to kill Van Ness. How was Bobby turning vengeful over the course of a few weeks of being dead, when Victoria had been dead over a century and wasn't vengeful? Also, in an early season there was a ghost of a woman who didn't know she had died and she'd been dead for like 20 years and wasn't vengeful. So, the Bobby "vengeful" ghost story arc really seemed forced because you can point to more than one example in the series where there were ghosts that never turned vengeful who were dead for decades or even centuries.
Plot hole: In season 8 episode 1, we find out that Dean has been trapped in purgatory for the last year. However, when Dean emerges back on Earth his hair is still perfectly styled, cut, and groomed. His hair is still gelled after a year, nor has his facial hair grown any longer.
Character Contradiction: In Season 8, Dean emerges from purgatory where he was for a year and is deeply angered to find that Sam had stopped hunting, found love, and was living a normal life. However, the fact that Dean was mad at Sam because he gave up hunting makes Dean a total hypocrite. After all, Dean did the exact same thing in Season 6 when he stopped hunting to lead a normal life with Lisa and Ben after Sam was sacrificed to stop the apocalypse. Why was it ok for Dean to lead a normal life, but not Sam?
Interesting Note: Am I the only one who noticed that former Detroit Lions Head Coach Jim Schwartz looks like an old version of Dean Winchester?
Dean stops hunting and does not look for Sam in season 6 because Sam makes him promise not to look for him
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