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[100deaths_a_day]

IC Information:

Character Name: Dean Winchester I refuse to list all his alias' as there is not enough space in the world

Character Journal: 100deaths_a_day

Canon: Supernatural

Point in Canon: 6.05 "live free and twi-hard", just after he cuts the nest leader's head off.

Age: 32

Birthday: January 24th

Appearance:





Because of his lifestyle, he has minor scars over his body, but nothing that is particularly mentionable, or visible unless he makes a point of mentioning them (which he doesn't). I should probably note he's very fucking tall 6'1".

Abilities: Before he was turned, he has no magical/psychic abilities. However, Dean possesses excellent combat and hunting prowess; comprehensively trained by his father from early childhood as a paranormal investigator and hunter of the supernatural, he is established throughout the series as an extremely dangerous individual, and he is more than capable of taking a stand against even the most formidable of opponents, such as demons and vampires.
Dean is well-versed with multiple types of firearms; he prefers his Colt 1911 and sawed-off shotgun, but is proficient with most other weapons he might acquire. An expert marksman, he seldom misses his intended target and can efficiently put down anything vulnerable to bullets.
Dean is adept with martial arts and knife fighting as well; he has subdued several human assailants with ease in multiple episodes and bested physically more powerful creatures, often unarmed or equipped with only a blade. In "Nightshifter", he killed a shape-shifter armed with a simple silver letter opener. In "Fresh Blood," he managed to subdue a vampire long enough to inject her with a shot of "dead man's blood." In "The Magnificent Seven," he fought and held off several demons by himself, armed only with a flask of holy water.
Dean is also a proficient tracker and possesses prudent tactical skills and an instinctive ability to "read" behavioural characteristics and manipulate people. Highly resourceful, he frequently utilizes improvised weapons and explosive devices; in "Croatoan," he demonstrated knowledge in chemistry constructing Molotov cocktails and improvised explosive devices, and in "Phantom Traveller," he revealed knowledge of electronics and reverse engineering, having built an electromagnetic field detector from an old Walkman radio.
Dean also possesses extensive knowledge of the supernatural and mythology. He is versed with how police, fire departments and various government agencies (FBI, CDC) typically operate and conduct investigations, and knows how to both impersonate and evade them effectively. An accomplished mechanic, he maintains his Impala in tip-top condition and has had an intimate knowledge of auto-mobiles and engines since childhood.
Dean is a virtuoso of escape, evasion and silent movement, when the situation requires subtlety and stealth. Lastly, he is also alarmingly skilful in many areas frowned upon by the law: lock picking, breaking into security systems (not so much computers, which often falls to Sam), car-jacking and gaining an 'advantageous purchase' comes naturally to him.
Due to his time spent in Hell as Alistair's "student," Dean has an in-depth knowledge of torture, able to inflict the maximum amount of pain and agony on a victim while keeping them alive as long as possible. In the Season 5 premier, Dean revealed he had learned the banishing spell that sends angels back to Heaven from Castiel.
Since he has been turned, he has increased strength, speed, hearing, agility sense of smell, and a set of retractable teeth. His skin is hurt by sunlight, but not burnt, and the only way to kill him is cut off his head. He has been shown to be superiorly fast and strong, even amongst vamps, in canon - taking out an entire nest of over fifteen vampires by himself, armed only with a machete
.

Personality:On the surface, Dean is a laid back type of guy who enjoys women, drink, and food - that is when he isn't chasing after some crazy demon, spirit, or anything supernatural. When chasing supernatural beings, Dean can become very serious about his job, and things that he must do in order to complete his job, although he appears to enjoy it.

Although Dean can sometimes become angry around certain discussions or insults about his family and his past, he has a sensitive side - even though that is shown more to strangers (especially kids, whom Dean can get a great rapport with) than his brother. He even sometimes questions himself about what would have happened if his mother never died. Things such as these can leave Dean in a angry attitude, and he normally picks fights with others around him (or his car) during these mood swings. He is remarkably adaptable when it comes to fighting and killing stuff.

Sam describes him as having the humour of a nine year old. He proves this in the same episod eas this is claimed, by putting a whoopee cushion on the chair that Castiel sits on. Sam describes Dean's taste in music in the first episode with the words: “The best hits of mullet rock” - but Sam still joins him singing “Wanted Dead or Alive” by Bon Jovi when they are being hunted down by hellhounds. He also rocks it out to “Eye of the Tiger” when he gets a disease which makes him scared of everything.

Over all, Dean is an action man,very impulsive and passionate about fighting the good fight. He trusts his instincts to lead him in the right direction where as his brother prefers to think things through before acting. He’ll kill without question and can be ruthless and aggressive at times. Despite mercilessly teasing and often arguing with Sammy, Dean loves his brother and would do anything for him, even going so far as to sell his soul to a demon which resulted in him going to Hell. Now that he’s escaped the pit, Dean’s fun-loving, carefree attitude has suffered a decline (though his womanising ways don’t appear to have changed) and soul destroying guilt has replaced it. He tries not to let it show but sometimes memories of Hell become overwhelming and his self worth is lower than ever before. In an effort to deal with that, he’s become a heavy drinker and wishes that he didn’t have to feel anything any more. Not that alcohol will do much to him now that he has a vamp constitution.

Being a vampire doesn't change any of these aspects of his personality - he's still Dean and acts in every way that makes him Dean. But he will, at firat, be slightly more withdrawn due to the fact he will be struggling with the bloodlust. He would not kill just to kill, as some vamps do, and he will be only eating when necessary, as it goes against his grain to hurt people that don't deserve it, and are “innocent”.

Strengths: Highly trained in combat, stealth and tactics thanks to his Marine father.
Has an inbuilt instinct for hunting and tracking.
Excellent marksman, well versed in all kinds of weapons
Very experienced in escapology under pressure
Expert driving skills gained from a life on the road, used for getting away from the law in a hurry and evading things that are about to kill him
Fearless and determined to protect the innocent and vanquish evil
Loyalty to family and friends
Can ‘read’ people, is good at judging character
Proficient with mechanics and knows a thing or two about chemistry
Very resourceful and opportunistic which makes him a smooth con-man
Good at not being seen when he doesn't want too
Now has new and improved vampire strengths: can see in the dark, improved vision, has improved sense of smell and hearing, strength, speed, agility

Weaknesses:His little brother, Sam
A stubborn and ever so slightly arrogant attitude that often gets him into trouble
A tendency to throw himself into the line of fire without really thinking about consequences - especially for friends and family
Can’t shake memories of Hell which make it difficult to get a good nights days sleep
Flying
Not being able to share his feelings with Sam - often leading to destruction Oh the impala, the poor poor Impala... or crying (but that usually passes quickly)
He gets antagonistic when he's pissed off, or in trouble - his smart mouth often making things worse for him
Bloodlust. And more importantly, not giving into it. He will fight it to the point where he is weakening - and even then, may try to fight it, unless someone shoves it under his nose (in a metaphorical, as well as literal sense).

History:1983: The Journal mentions that prior to Mary's death, Dean played T-Ball.
November 2, 1983: Mary Winchester is killed by Azazel when she interrupts him feeding demon blood to Sam. John hands the infant Sam to Dean as the nursery burns and tells him to "Take your brother outside as fast as you can! Don’t look back! Now Dean, go!" John leaves Lawrence with Dean and Sam before Dean's fifth birthday.
1985-86 (approx): When Dean is "6 or 7", John takes Dean out shooting for the first time, using bottles as target practice. According to Dean, he "bullseyed every one of them." Dean cites this story as one of the fonder memories of his father.
1989 (approx): John is hunting a Shtriga in Wisconsin and leaves Sam and Dean alone in a hotel room. Dean gets bored and goes out, and comes back to find the Shtriga attacking Sammy. John returns in time to scare the Shtriga off. Dean is haunted by his failure to defend his brother.

1991 (approx): When Dean is in sixth grade he makes his first sawed-off shotgun.
Christmas Eve 1991: Dean is left to babysit Sam (8 years old) while John is on a hunt, and Sam begins to interrogate Dean about what it is that their dad actually does. Dean responds "You know that. He sells stuff." When Sam moves on to asking about their mother, Dean gets angry and yells "Shut up! Don't you ever talk about mom! Ever!" before storming out. Upon his return, Sam reveals to Dean that he found and read their dad's journal, and demands to know if monsters are real. Dean finally resigns himself to telling Sam the truth.
Dean: I swear, if you ever tell dad I told you any of this, I will end you.
Sam: Promise.
Dean: First thing you have to know is...we have the coolest dad in the world. He's a superhero.
Sam: He is?
Dean: Yeah. Monsters are real. Dad fights 'em. He's fighting them right now.
It is hinted at that Dean still believes that his father is a "superhero" at this point, and continually excuses his flaws, while the tension between Sam and John is clearly starting to take root.
Disappointed with John's lying and absence, Sam gives Dean the present intended for his father: the amulet that Dean never takes off.

1995: Dean is 16. He injures and kills a vampire. As told by Dean to fellow hunter Gordon in 2.03 Bloodlust:
Dean: ... So, I picked up this crossbow, and I hit that ugly sucker with a silver-tipped arrow, right in his heart. Sammy's waiting in the car and, uh, me and my Dad take the thing into the woods, burn it to a crisp. I'm sitting there and I'm looking into the fire, I'm thinking to myself... I'm sixteen years old. Kids my age are worried about pimples, prom dates... I'm seeing things they'll never even know. Never even dream of. So right then I just sort of...
Gordon: Embraced the life?
Dean: Yeah.

Fourth of July, 1996: Dean rebels against his dad and takes Sam out to a field. End result? They accidentally burn it down.

1997: In summer 1997 John, Dean and Sam are hunting a werewolf. In November 1997, John "parks" the kids in a small town in Iowa, where they attend Truman High School. While Sam is having trouble with a bully called Dirk, Dean gets a girlfriend, Amanda, although he becomes uncomfortable when she wants him to meet her parents. When she catches him cheating on her with another girl, she challenges him, charging that his 'cool' persona is a cover for his loneliness.

1998 or 1999: He's 19 or 20. Dean goes on a road trip that was supposed to be "5 states, 5 days" while Sam (15 or 16) was "in Orlando with dad, wrapping up that banshee thing". However, Dean spent most of his time in Lisa Braeden's loft - "She was a yoga teacher. It was the bendiest weekend of my life."

Sometime between 2001-2005: Sam leaves for Stanford. While there he becomes estranged from Dean and his father, and doesn't speak to them for at least a couple of years.
During this time, as Dean tells Sam in “Route 666”, he met Cassie Robinson while he and John were in Athens, Ohio for a hunt. She was "finishing up college" and they "went out for a couple of weeks". Dean was in love with Cassie, who was the first person he'd ever seriously dated (as Sam says "for more than one night") and the first person he'd ever felt that way about. When he found out he was leaving, he told Cassie the 'big family secret' about hunting because, as Dean says in the episode, he "just couldn't lie to her". Cassie, however, called him 'nuts' and dumped him. This, as Dean also revealed in the episode, really hurt him, and he decided at that point that it was "stupid to get so close" and that he didn't need to open up to anyone.
Note: It is likely that it was around 2003 or 2004, during the "almost two years" that Dean did not speak to Sam, because Sam claimed that Dean hadn't told him anything about it. That means Dean was approximately 24 or 25.

October 2005 :When Sam asks Dean why he didn't go with John when he left to check out the hunt in Jericho. Dean explains that before he showed up in Palo Alto to get Sam from Stanford, Dean was "working my own gig ... this, uh, voodoo thing down in New Orleans". Sam asks, "Dad let you go on a hunting trip by yourself?" to which Dean replies, "I'm twenty-six, dude." This implies that before Sam left for college when Dean was 23, Dean had not gone on a hunting trip by himself. Considering the two men had not spoken in "almost two years", as Dean points out in the pilot episode, it could mean that Dean hadn't hunted alone until he was 24 or 25.

From an early age, he was trained by his father John Winchester to hunt down and kill things of the supernatural, but unlike his brother he shows no resentment toward his father for being "raised like a warrior", feeling that after his mother's violent death, his father raised him and his younger brother the only way that he knew how at the time. He seems to prefer "the hunt" to the possibility of a normal life. Due to his father's training, he has several notable advantages for a human: he is an exceptional shot, has knowledge beyond the norm regarding the supernatural, is a skilled fighter, and appears to have some proficiency with melee weapons. He is also the only one allowed to call his brother "Sammy". When giving false names, he frequently gives the names of rock musicians. He also appears to be a fan of Jack Nicholson and Stephen king (if you go by his references, and the amount of them), and possibly watches Oprah. He tends to make light of some of his and Sam's adventures and is known to use crude humour, make sexual innuendos and indulge in pornography. He has only been in love once and avoids any emotional intimacy preferring to just keep women as sexual partners. The handful of women who become his friends usually give him a hard time and keep him in line. He is devoted to the memory of his mother and his younger brother Sam. He is also a passionate defender of humanity. He is terrified of flying and claims that it is the reason why he drives everywhere. 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.
Season 1
When Dean was four years old, his mother Mary was killed in his younger brother Sam's bedroom. Twenty-two years later, The Demon responsible for their mother's death kills Sam's girlfriend, Jessica Moore. Together, Dean and Sam go on a road trip to fend off supernatural creatures and search for their father, John, who occasionally leaves new missions for them to complete.
Early in the season, Dean and Sam battle a shape-shifter responsible for a string of brutal murders in the St. Louis, MO area. During the course of the episode, the shape-shifter assumes Dean's form, causing police to believe that Dean is responsible for the murders. However, Dean kills the shape-shifter while it is still in his form, and the authorities officially declare him dead.
In the last episode of this season "The Yellow-Eyed Demon" possessed Dean's father in an attempt to get The Colt for his own. After Dean realizes this, The Yellow-Eyed Demon pins him and Sam to a wall and reveals that John favors Sam over Dean. The demon also tells Dean that he was responsible for sending his children back to hell, after Dean makes a sarcastic remark about the situation, the demon tortures him, Dean pleads for his father's help before losing consciousness. Sam manages to get free and shoots the demon/John in the leg, releasing the demon from John's body.
The season finale concluded with Sam, Dean, and John escaping from a clash with The Yellow-Eyed Demon in Salvation, Iowa. While Sam was driving to a hospital after Dean and John were injured, a demonically possessed driver drove his truck into the Impala, causing massive damage to the car and the Winchesters inside.
Season 2
All three of the Winchesters survive the wreck, although Dean is more severely injured than his father or brother. In the first episode of Season 2 ("In My Time of Dying"), Dean is in a coma and, in order to save him, John makes a deal with The Yellow-Eyed Demon, trading his life for Dean's. Before he dies, John whispers something in Dean's ear which the audience cannot hear.
Throughout the first half of the second season, Dean struggles with the death of his father, as well as with the knowledge that he was the one who was supposed to have died. Furthermore, he is haunted by his father's last words to him, and at the midpoint of the season, it is revealed that John told Dean that The Demon intends to turn Sam evil, and if Dean can not save Sam, Dean must kill his brother.
During an investigation in Baltimore, MD ("The Usual Suspects"), Dean is arrested in connection with another series of murders. It is revealed that Dean has a rather impressive police record, with charges over the years including credit card fraud, breaking and entering, and grave desecration. Although Sam and Dean are able to prove that the murders were actually committed by one of the detectives on the case, it is unclear whether or not the charges against Dean were ever officially dropped. However, the problem still remains that the authorities have realized that Dean is not dead, as they had previously believed. A team of FBI agents, led by Special Agent Victor Henricksen catches up with Dean and Sam in Milwaukee, WI, where attempted bank robbery and several more murders are added to Dean's list of supposed crimes.
At the end of All Hell Breaks Loose - Part 1, just as he arrives to rescue his younger brother, Sam is stabbed and collapses into Dean's arms. Amidst his brother's pleas to stay with him, Sam dies, leaving Dean alone as the last living Winchester. Dean, believing he failed Sam, is too upset to deal with the crushing blow delivered when Sam died, and in a last ditch effort travels to a crossroads to make a deal with the "crossroads demon" for Sam's life in exchange for his soul. In the end Dean is allowed one year to live and Sam is then resurrected. At first, Bobby Singer is the only one to know of what Dean did, because Sam can't remember anything past when Jake Talley stabbed him and Dean makes up a lie about Bobby patching him up. Bobby yells at him for what he did and Dean pleads with him not to tell Sam what he did, as he knows it will destroy Sam knowing Dean sold his soul.

Dean questions if what he brought back in Sam is “pure" after Sam unhesitatingly kills Jake, unloading several bullets into his head without any sign of remorse. When Sam figures out what Dean did, and Dean tells him not to be mad, that he couldn't let Sam die, not like that. At the end of the second season Dean kills The Yellow-Eyed Demon with the Colt freeing his father's soul but during the battle hundreds of other demons escaped their prison and now Dean and Sam must kill all of them, as well as find a way to save Dean from dying in a year's time.
Season 3
In the season premier of season three "The Magnificent Seven", Dean makes the best of his last year, not worrying about his safety - to the point he acts foolishly and almost self-destructively. while Sam tries desperately to find a loophole in the crossroad demons deal. After continuous arguments with Sam, Dean tells Sam if they try to wiggle out of the deal, Sam immediately dies. The brothers also meet Ruby, a demon who supposedly knows how to free Dean.
Towards the end of the season, Dean discovers that the demon, Lilith holds his contract.
Dean, with 30 hours left, stills desperately tries to free himself. He uses his last resource, Ruby, and takes her demon-killing knife. With help from Bobby, he discovers Lilith is in Indiana. While the trio head to Indiana, Dean discovers he can see who is possessed and can see demons, such as Hellhounds. As the clock strikes midnight, Dean smiles and tells Sam to be brave and to continue what he's doing. Sam watches as his brother is mauled to death by the hellhounds, pleading Lilith to stop. Now in "Hell", Dean is desperately yelling for help, calling out for Sam.
Season 4
In the season premiere "Lazarus Rising", Dean escapes Hell and reunites with Bobby and Sam. At first, he doesn't know who or what brought him back. With help from Pamela Barnes, a psychic, he finds out a supernatural being called Castiel has surfaced him.
In "Are You There God? It's Me, Dean Winchester", Dean is haunted by the spirits of Meg Masters, Henricksen and Ronald Reznick, wanting to kill Dean for not saving them. Dean, with guidance from Bobby, ultimately puts their souls to rest.
"In The Beginning", takes Dean to 1973 where Dean learns about the Winchester history. Although tempted to stop Azazel from killing his mother, he realizes that he and Sam will no longer be hunters and all the people they saved will die. Dean learns that his mother was a hunter, too. Teaming up with his future mother and grandfather, they plan to take out Azazel with a borrowed Colt. Dean fails to stop him and the demon finds John about to propose to Mary. Samuel kills John. A tempted, heartbroken Mary confirms a deal with Azazel, allowing him "permission" in 10 years. Dean arrives shortly and realizes he can't change destiny.
Dean learns about Sam's new powers in "Metamorphosis" and learns that Ruby is back. He freaks out and tells Sam that he's not human and that if he wasn't his brother, he would kill him.
After the two reconcile, they tackle a shape-shifter in “Monster Movie", a ghost in “Yellow Fever", an old and powerful demon in “It's the Great Pumpkin, Sam Winchester”, and the after-effects of a cursed coin in Wishing Well before they encounter Ruby again. Dean, throughout the I Know What You Did Last Summer learns what happened to Sam in the four months that he was in Hell.
Dean, along with Sam and Ruby, defend Anna Milton from Castiel, Uriel and Alastair as both Heaven and Hell want Anna for their own personal gain.
Both Dean and Sam overcome new obstacles such as fighting an abandoned girl in Family Remains, defeating a tricky Magician in "Criss Angel is a Douche Bag", facing his past in "After School Special" and killing a seductive Siren.

In "On the Head of a Pin", Dean is brought in to interrogate Alastiar, who the angels think is killing other angels. After refusing, Castiel begs Dean to do it. Eventually doing it, Dean discovers who it is. Dean, however, is fatally injured, after Alastair breaks free and attacks Dean. Dean awakens from a hospital bed and tells Castiel that he doesn't want to stop Lucifer anymore. He also discovers he is the one the who opened the first seal. Castiel tells him, "The Righteous Man who starts it, will be the one who finishes it."
Dean deals with many other obstacles including the superior, stubborn angel Zachariah and the prophet Chuck Shurley.
Towards the end of the season, Dean and Sam have a strong confrontation which leads into a seperation. Dean telling him never to return. He swears his alliance to serve Christ and is then held captured as Zachariah prevents him from stopping the Apocalypse. After being freed by Castiel, he finds Sam, only to realize he's too late. Before killing a back-stabbing Ruby, Sam kills Lilith, and in doing so, brought on the Apocalypse.
Season 5
The fifth season begins right where season 4 ends with the portal opening. As Lucifer escapes, the brothers are teleported into an airplane by an unknown force (later revealed to be God). Dean is told by Zachariah that he is the "Sword of Michael", which means the Archangel Michael will use his body as a vessel to lead the forces of heaven, but Dean must consent to this. Dean refuses and Castiel saves him when Zachariah tries to force Dean to agree by harming him and Sam.
Dean gets aged in “the curious case of Dean Winchester” by 25 years, after trying to save his friend Bobby.
Dean and Sam fight the Horseman War in a town where the people think that their neighbors are demons. In this town is Ellen, Jo, and Rufus all trying to hunt the demons, who turn out to be just people that War has made eyes seem black. Afterwards, Castiel finds Dean and they capture the Archangel Raphael to ask the location of God.
In the fourth episode of the season, Dean is transported forward in time - this time by Zachariah - to see what the future will be like. He finds himself in 2014, eventually meeting up with his future self, as well as the survivors and victims of the Croatoan virus from season 2. Dean finds out that Sam let Lucifer into his body, and this was the reason the world was in such disarray. Later, the future Dean is killed by Lucifer, while in Sam's body. After being told by his future self to accept Michael into his body, Dean is transported back to his own time, where he comes face to face with Zachariah. He refuses to become Michael's vessel. In the end of the episode, the brothers meet back up again, and decide that they should stay together, to "Keep each other human." In the episode “Changing Channels”, it is revealed to Dean and Sam by the Trickster (who reveals that he is the Archangel Gabriel) that their relationship (Dean, the older brother loyal to an absent father, and Sam the younger brother, rebellious to the father's plan) mirrors the relationship between Lucifer and Michael, and has been told to the angels since the beginning to bring about Judgment Day.

The tenth episode of the season shows Sam and Deans plans to find Lucifer and kill him, with help from Castiel, Jo, Ellen, and Bobby. The Winchesters later find out that Lucifer is one of the five things in the universe that the colt cannot kill by using it on him, with no effect. Having lost another plan, Dean becomes more disillusioned and hopeless, and with his experience in Heaven during "Dark Side of the Moon" where after spending time in heaven and finding out God doesn't see the battle with Lucifer to be his problem, he begins to see little reason to deny his destiny as Michael's vessel, deciding to take on the role at the end of the next episode.
During "Point of No Return" he was preparing for his possession by Michael before being discovered by Sam and Castiel, who return him to Bobby's house. They convince him to allow them some more time in order to research another method of stopping Lucifer; however the unexpected resurrection of their brother Adam Milligan, planned to be a vessel, forces Sam, Bobby and Castiel to keep Adam and Dean from Zachariah. When Dean escapes and tries to lure the angels, both Castiel and Sam leave to find him, allowing Adam to be removed by Angels. Despite Bobby and Castiel's insistence in keeping Dean from Zachariah, Sam allows him to try to rescue Adam. With Castiel removed, along with the angelic guards, the brothers attempt to rescue Adam, but Sam's ambush on Zachariah fails and Zachariah causes internal damage to both Adam and Sam to coerce Dean to consent to Michael. Ultimately, he relents, but after Zachariah summons Michael, Dean taunts him into sacrificing himself in order to allow Michael in. Zachariah angrily refuses, and Dean stabs him and rushes out, unfortunately leaving Adam locked in the room with the approaching Michael. As they leave, Dean admits that he would have accepted Michael, but because of Sam's faith he decides that he will "take the fight to them".
Dean is about to lose hope until Castiel and Bobby help pull him back together and he goes to the battlefield and interrupts the destined battle between Lucifer and Michael. Dean gets beaten t a bloody pulp by Lucifer. Castiel heals Dean and the apocalypse is finally over. Dean is outraged by the outcome as he lost Sam again but Castiel tells him he got exactly what he wanted and then vanished to restore order to heaven as Michael is gone now. Dean goes to live with Lisa and Ben.

I'm also going to mention that he also takes Castiel to a brothel in this season, claiming that he does not want his friend to die a virgin, and he finds the results hilarious.
season 6
One year later, Dean is living a normal life with Lisa and Ben, having a normal job and having the Impala covered up with his weapons locked away in the garage. He is truly happy until he notices supernatural occurrences around his neighborhood. He is reunited with Sam. They are filled with joy to see each other again but Dean is soon enraged when he figures out that Sam has been back this entire time and didn't tell him. After the crisis of the episode has been averted, Sam leaves and Dean decides to take care of Lisa and Ben and continue on with a normal life while Sam goes back to hunting. Dean offers the Impala to Sam but he declines as he has his own car now and tells him to keep in touch.
Dean relocates Lisa and Ben to a different home and starts to take on traits of his father that were similar in his childhood. Dean is soon conflicted with either leaving and go hunting with Sam, or stay with Lisa and leave that life behind for good. Then Lisa suggests a compromise, he can go hunting and come back whenever he can. He agrees and gets the Impala out of the garage and gets back on the road with a smile on his face.
Sam joins Dean again when his car gets destroyed.
Deaths and Dean's had a few:
Through the course of the series, Dean has died many times. He died in Season 2, but is brought back by defibrillation. Then, as he has just accepted death and is about to die again in that episode his father makes a deal with Azazel to bring him back. In the episode "Mystery Spot", Dean has died over a hundred times. All in a completely different way which includes being shot, hit by a car, poisoned, choking, vicious dogs and a lot more. However, whenever Dean dies, the day starts over again. They find Trickster is behind this game and forces him to stop. Trickster tells Sam that this is how it's going to be like after Dean dies and it he can't do anything to protect Dean. In Season 3, Dean has almost spent his year. Desperately trying to find a way out, he goes after Lilith, the demon holding his contract. The attempt fails and Dean is viciously mauled by Hell Hounds.
In Season 5 he dies again, killed by hunters in search of Sam (who is also killed). Also, He's a vampire -technically dead.

First Person Sample: [He put his foot on the vamp's head, and looked up from where he was stood. But... the oddest thing happened. He was no longer in the room where the body lay. He was now in a room that was empty save for him, and the body-less head under his foot. He also had no clue he was being recorded by the blackberry device on the side.]

...Where the hell am I? and more importantly, how will I get the damned cure now? [he growled as he took his foot off the vamp's head, and kicked it away from him in frustration. It's then that he notices the blackberry, and comes and picks it up. Then he notices that it's recording.]

Does somebody want to tell me what the hell's going on?! Where am I, and how did I get here? ...And more importantly: Does anyone know a Sam Winchester? [If he could find Sam, they could figure this out, and get him the cure. He just had to not feed... which would be great, if it weren't for all the hearts he could hear beating in the place he was now in. Screw it, he was strong enough.

He had to be.]

Third Person Sample: He could hear the blood pumping from the person in the room with him. The light was too bright, it was hurting his eyes a little. But he'd adjust to that, he knew that. The ticking of the clock was loud, and it was grating on his nerves. “I swear to God, shut that damned thing up, or I will.” He growled. His irritability, and current condition made it come out... animalistic. That surprised him, though.

The pounding of the other heart in the room, the wet thump-thump-thumping stirred his hunger. He had to get out. Go somewhere, anywhere. Escape that which was going to drive him insane. Either that, or to feed. And neither was a good thing. He stood,a dn when challenged, he responded irritably “Even vampires have gotta take a leak.” Not that he did. He shut the door, and wrenched apart the blinds, and opened the window quietly. Quietly to human ears, at least. The sound echoed through his head. This was all just like a bad trip.

He looked back over his shoulder to the window, sighed quietly, and jumped, landing spryly on his feet, despite having just jumped from three stories out of a bathroom window. But Dean was trying not to think about the perks. Just on not hurting or eating anyone.

With that last thought, he headed off into the new world of smells, sounds, and sights that surrounded him.

Links:
here and here

Notes: there's not enough shirtless!Dean in canon any more Nope, not that I can think of.

Bonus: BECAUSE I'M A DINOSAUR. RAWR.