Welcome back to Bookstr’s Literary F*ck Boy Tinder profiles! Today we are here to bring you one of the best hunters in the world. He’s the killer of demons, angels, ghosts and monsters alike; a pie enthusiast, famous FBI impersonator, Mark of Cain wearing, should just come out as Bi already, Scooby-Doo loving heartbreaker, over the shoulder thirst trap extraordinaire; Dean Winchester!
If you somehow don’t know, this handsome, handsome man, Dean Winchester is the eldest of a supernatural monster hunting team with his brother Sam Winchester on the long running CW show (and subsequent book series), Supernatural, which is in it’s final season. I’m devastated but it’s time.
But we aren’t here to be all sappy, we’re here to discuss this man’s f*ck boy behavior! And the endings to his more serious relationships.
Whether he comes across a nest of vampires, packs of werewolves, leviathan, or Death himself, he’s usually always down for a hookup with a beautiful woman he met at a small town bar or one of their female clients if he can. He even has been show to have a dating profile on the show.
‘Rolling through town, no strings attached’ is right! Dean is known for hooking up literally all over the country as he and his brother travel to defeat some source of evil somewhere. However, unlike or last f*ck boy, Damon, Dean has had a few more meaningful relationships through out the show’s run.
The major relationship of note was with Lisa Braeden, where we met here in season three. The two met while Dean was hunting solo and spent a week together before he had to leave town. They meet again but now with Lisa was her nine -year-old son Ben, who isn’t Dean’s but becomes like one in the future. At the end of season five and into season six, Dean lives with Lisa and Ben and had been for a year after Sam died (not for long) and retired from hunting.
When he comes out of retirement and it is reveled Sam is alive their relationship started to crumble. Their relationship finally and unfortunately ended when he had Castiel take her memories away to keep her safe. I’m still crying!
His first love interest was Robin when Dean was sixteen. Their relationship ended abruptly when he couldn’t keep his promise to take her to the homecoming dance because the boys’ father forced them to hit the road again. They met again years later but didn’t get back together due to “the family business”.
Another short lived relationship is with Anna Milton, who we met in season four of the show. Their relationship was very short lived after she tried to kill John and Mary (Dean and Sam’s parents) in the past before his brother was born. She is killed off by the angel Michael.
Next, we have Cassie Robinson. The two met while she was in college and he was on a job in Ohio. This is one of the only women he trusted with the true nature of his job. She was understandably freaked out and dumped him but was still very much in love with him.
Dean has a lot of parental issues. If you know, you know, child! The show has never shied away about how hunting and keeping up with “the family business” affected the brothers. It’s no more evident in their romantic relationships. Many of Dean’s relationships, booty calls excluded, have been impacted by the grand design of Dean and Sam being the be all, end all, to the save world. The one true love of his life, Lisa had to be made to forget him because he didn’t want his life to change hers anymore than it already had.
Before we go, we must talk about Dean and Castiel’s long shipping. Castiel is an angel who becomes more than just an antagonist for our boys, he becomes a great friend, ally, and is referred to as family from time to time. BUT, we the fans couldn’t help but notice the intense chemistry between the two.
Many jokes have been made about the Destiel ship in the show as the creators and actors are in-tune with the goings on of the fandom. For me personally, you can’t erase the tension that has been built up between the two, so whether the writers had always had intended these underlying feelings for the characters or not, they have the best bromance of all time.