He doesn't come across as talkative, but a solemn type who gets on well with Rory. S03E16: Dean's second death (Of course, I've skipped over every death involved in S3e11 "Mystery Spot," as those were non-canon-timeline deaths. Dean is the new kid in town at first, having recently moved to Stars Hollow from Chicago in autumn 2000. Dean Winchester is one of the two main characters of the TV series, Supernatural. Dean plays softball, hockey and hangs out with … He quickly notices Rory and the two embark on a long romance, which culminates in Dean cheating on his wife with Rory in 2004. Initially, Dean is a cute, smart, witty guy, who seems kind and down to earth. After spending a year trying to subvert the deal Dean made with Hell unsuccessfully, Sam finally has to watch Dean get ripped apart by hellhounds on the hunt for his older brother's blood. At the end of Season 2, he makes a deal with a demon to bring his brother Sam (the other main character) back to life, and in a year, Lilith (the holder of all demon deals) will send hellhounds to kill him and take him to Hell for eternity. Be glad.)

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