Dean Winchester

Dean Winchester is a character from the Supernatural fandom. He is played by Jensen Ackles.

Biography
Dean Winchester was born on January, 29th 1979 in Lawrence, Kansas to John and Mary Winchester. He is Sam Winchester' s older brother by four years. Following the murder of Mary Winchester by the demon Azazel on November 2nd, 1983, John handed over the responsibility of raising Sam, who was six months old at the time, to Dean. This protectiveness has lasted their entire lives, and has been the cause of many arguements between the Winchester boys.

As John begins to investigate Mary's death and subsequently learns about the supernatural beings in the world, he begins to hunt them. As a result, Dean and Sam are hunters from a young age. The Winchester constantly moved around the country, living in motels and houses of other hunters. When Dean was 16, he was arrested for stealing food while John was away on  a hunting trip and spent time in a boy's home where he had the chance to go to a regular school, but ultimately gave it up due to return to John and, more importantly, Sam.

Dean is known for being able to handle a large amount of weaponry. He is commonly seen in a dark leather jacket, dark shirts, and dark jeans. He is also known to drive a black 1967 Chevrolet Impala Sport Coupe, which he keeps a stash of hunting paraphernalia hidden in the trunk.

Destiel
Destiel is the ship between the angel Castiel and Dean Winchester. Castiel first appeared in season four of Supernatural when he pulled Dean from hell. Their relationship has been referenced on the show and is  supported by a large chunk of the fandom. Misha Collins, the actor of Castiel, has even made jokes about it at conventions and on his twitter.

A masterpost of meta about Destiel can be found here.

Wincest
Wincest is the cleverly named ship between Sam and Dean Winchester. The brothers have been shipped since the beginning of the show and this relationship has been referenced on Supernatural on several occasions.

A collection of meta about Wincest can be found here.

In Canon
Dean Winchester is the definition of a womanizer, though there have been instances in which his interest towards men has been prevalent. His relationship with women is not healthy, his longest relationship lasting a year with a woman named Lisa that he only knew because of a "bendy weekend" years ago. Many fans have smeared their relationship as an excuse for Dean not to focus on the important things that were going on at the time.