Dean Winchester

Dean is shown to be understanding, kind, funny, mischievous, and, in contrast to his younger brother, a little immature. At an early age, Dean was trained by his father, John Winchester, to hunt and kill creatures of the supernatural. However, unlike his brother Sam, he did not resent his father for having him "raised like a warrior". He seemed to prefer hunting the supernatural over any normal "apple pie" life, though it was revealed that when he was sixteen, he did in fact desire (or at least hope for) a normal life: He just couldn't leave Sam. This however did not last long, as later on while still sixteen, following a werewolf hunt he realized just how unique his life was. However, by Season 7, following all that he has seen and done, Dean admits to Eliot Ness that he no longer wants to be a hunter and would give it up if he could.

Dean is an avid fan of classic rock music. Many of his aliases have included the names of famous rock musicians. He is known to use crude humor, make sexual innuendos and indulge in pornography (especially for Busty Asian Beauties). Dean typically avoids emotional intimacy, preferring to engage with women only as sexual partners. However, he has had a few long term relationships over the years, with Cassie Robinson, pre-series, and Lisa Braeden, in Season 6. After the tragic events that led Dean to ask Castiel to make it as if Lisa and her son Ben had never met him, Dean seemed to give up on ever having a family other than his brother.

Dean values his family's safety over anything else, even going so far as to kill a demon and its human host in order to save Sam's life, as well as sacrificing his very soul and suffering in Hell to resuscitate his brother. When he discovered he had a half-brother named Adam Millagan, he didn't believe that his father had another son until he saw a frame of the two together. He begrudgingly accepted it and helped what he thought to be his brother. When he met the real Adam, Dean didn't want him to suffer as a vessel for him and apologized to him after that failed. When he met his paternal grandfather Henry Winchester, he resented him for leaving his father as a child until he realized it wasn't his fault and apologized for it.

Dean is typically ruthless and aggressive when he is hunting, a task which he approaches enthusiastically, making him the more merciless of the Winchester siblings. But in spite of that, he is capable of acknowledging whenever he's going too far, as seen with his interaction with Lenore and Gordon. Whereas Sam is at least willing to sympathize with what they hunt, provided that their motives can be counted as morally gray, Dean mostly sees the world as black and white. He passionately despises what he hunts, especially demons, and is prepared to kill without question more often than not, unlike his brother. This has caused him to develop a bigotry against most supernatural creatures and beings.