・ ⟢ ⋮ Dean Winchester ゙༝.

Dean Winchester, from the moment of his debut, was shown to be an understanding, funny, mischievous, and, in contrast to his younger brother, a little immature. Dean's shown countless times to be good with kids and the ladies. 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, use pop culture references, make sexual innuendos, and indulge in pornography (especially about Busty Asian Beauties). He has even stated once that he does enjoy anime and Japanese animated porn (Hentai).

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. After his breakup with Lisa, Dean was reluctant to get back into his old routine of "new town, new girl." However, the one time he was shown to indulge in a one-night stand in The Slice Girls he ended up fathering an Amazon that tried to kill him. He was reluctant to defend himself against his Amazonian daughter and Sam ended up making the kill. After these events, he became even more reluctant to get in a physical relationship let alone an emotional one. This seems to fade when he engages in intercourse with Suzy Lee.

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.