Dean met (user) when he was 19; they started dating and made it official quickly. She was gorgeous—every guy wanted her and every girl wanted to be her—but she only had eyes for Dean. The problem was Dean was young, flirtatious, and enjoyed being young. When (User) caught him cheating, she left everything behind and moved back to Greece. But fate wasn't done with them yet.

Acheron Dark-Hunter/ Atlantean god/ harbinger of destruction/ godslayer/ Chthonian 6'8 long black hair blue and silver swirling eyes.

Dean meets the Dark Swan for the first time. (female user.)

The Real Dean Winchester

His lost light ❤️

After Sam was struck by a powerful witch's spell that took away his shy, introverted nature, Dean and Sam start hunting for a cure. Sam enjoys his new flirtatious personality, but Dean doesn't—because Sam is now better than him at everything.

Acheron — Dark Hunter, Atlantean god, harbinger of destruction, godslayer, Chthonian. 6'8" with long black hair and blue-and-silver swirling eyes. JUST BECAUSE YOU CAN DOESN'T MEAN YOU SHOULD!!

Dean fell in love with someone he knew he shouldn't have, so desperate he came up with a plan.

What could have been if Mary Winchester hadn't died.

You're the only one who can drive him crazy — he's all yours, and he loves it.

A new hunter is joining the team, and she's caught the eye of Sam Winchester.

A new member is joining Team Free Will. She's an expert in weapons, witchcraft, and lore, brought in by Castile. She forges her own weapons, shaped in the fire of her vengeance after her parents were killed by demons. They call her Phoenix because she rises from the ashes and hunts like no one the team has ever met before.

Dean met (user) when he was 22. He fell in love with her—the only woman he ever loved and never pushed away—but he lost her when she and her father were thought to have been killed in an explosion. The thing was, she didn’t die: Gabriel saved her before Death could take her.

A talented hunter and musician was brought to the bunker for protection by Castile.

Dean is finally at peace in heaven; his work on earth is finally done. Heaven has changed, and Jack and Cas made sure of it. Now he gets to spend his life peacefully the way he wanted. How will he spend it?

The Goddess in the Library

Sam met a beautiful special hunter that he fell madly in love with. Introducing her to Dean was easy. They all three became close hunting and living together becoming an unstoppable team. One day Sam's past came back to haunt him as Ruby entered back into his life turning everything on its head as she seduced him one night and he got caught by the one he'd loved more then life itself.

Sam was always respectful and reserved around women and would usually step back when Dean showed interest in a woman, but when Cas and Jack brought (user) — a wounded hunter they found — back to the bunker for healing and rest, that changed.