Dean and his LOVE of Women…….

One thing that put me off Dean, and took me a while to really understand him was his excessive obsession with women. Wanting to flirt with every women he nearly came into contact with. I don’t know where his obsession came from, was John a flirt or Henry Winchester.  Or was it on the Campbell side, was Samuel, Deanna, or other Winchester relatives real flirts? or does it stem further back than this in Dean’s family history. They say these things are hereditary? It was and still is an annoyance with me, and find it an off putting trait of Dean’s that doesn’t ease. So a question for Dean fans, does his obsessive obsession with women ever bother you?


Dean was almost ready to get his kit off, every chance he got? And had no problems with how he asked the chick to co-operate …. and is always confident in approaching women. His smooth, slick style never wavers, and his chat up lines and looks melt any girls heart like a spider in a web, a female caught in the strands weighting to be eaten by its prey.

In the event of side lining his little bro Dean went off the beaten road for a little love, in a shady motel room, only for little Sammy to walk into the room catching a spot of the action, that he’s never forgotten …..

His Eyes on his latest Lady! His devotion to her is commendable, he lights up her life! And is drawn into his web and Dean sets his woven web into action. He stares into her eyes and uses that gleaming smile to attract her attention, and goes for the kill…..

Dean with his favourite porn star grinning from ear to ear, did she meet his expectations and did he have the time of his life? Was finding her in real life the best present he could wish for?

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In bed with the local bar maid, whom Demon Dean treats appallingly, just to have company for a time. Was it really the way to treat a Lady? Yes, Dean was a Demon would the real Dean do this, NO. It would be out of character. But I felt so bad for her, seeing the look on her face ….

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Demon Dean strikes again, with a Pole Dancer in front of his goggles. Is this as low as out of character Dean could GO! Why did this not surprise me, having sensed DD would end up with a Pole Dancer, thinking this was NOTHING NEW to his character. Is Demon Dean that far different from the real DEAN is some ways?

We all know that Dean loves his bed, but who does he end up with?

Where does his heart REALLY lie?

Does he LOVE one night stands so much, that it means he finds it hard to commit to a long lasting relationship?

Hopping from one bed to another, what does this say about a person? Does it clarify who they really are?

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25 thoughts on “Dean and his LOVE of Women…….

  1. Love this article, Bella.

    I never had a problem with Dean loving women. It’s actually a trait I absolutely love about him, and a reason I’m constantly annoyed with those who want to turn him into a monk or force him into a same-sex relationship in canon. He loves posse. He’s a posse magnet. Make that into a t-shirt and deal with it.

    I don’t see anything wrong with what he’s doing. He’s drop-dead-gorgeous, smooth and the women are willing. Remember your thread about favorite characters? I described Dean as sensual and carnal. He likes to eat, he’s voracious and not ashamed of it. I see him as a very healthy man who’s single and unattached and “well fed”. He wants a burger, he eats it. He wants sex, he finds it. He’s not forcing himself on anyone or leaving a trail of fatherless babies in his wake.

    When Dean is in a relationship, he doesn’t run the streets. He had the option to cheat on Lisa and didn’t take it. He’s capable of falling in love and opening up. He told Cassie about who he was and wanted to see her again. Young Dean was a menace on the streets. With age, he calmed down some but he’s still Dean and virile as ever in his mid-thirties.

    If he got married, he would be as good a husband one can be when they’re glued to their brother 24/7. His womanizing never got in a way of him being a deep, complex and layered character. He’s the guy who can take the time to help a traumatized child find their voice again AND get a kiss from the kid’s mom before he hits the road. That’s what you call efficiency and multitasking. Don’t hate, appreciate lol.

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    1. Love this article, Bella.
      Thanks honey, it took a while to compose and laid my heart on the line and those are always difficult to write the most!

      See you understand Dean. I get this whole comment. Its turned me around and you’ve done you’re job amazingly well!

      He doesn’t cheat on those he’s in a relationship that is very, very true and he had the opportunity with Lisa and Cassie and Anna and he didn’t. More importantly with Lisa because he was with her the longest out of all of them. He is only on the look out when he’s not in a relationship. Kudos to the writers for that one! I am seeing our Dean in a different light already. I never hated Dean, just found it to be more of an annoyance. I certainly will appreciate it more now. Thanks Virile for turning me over to the light!

      B xxx

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      1. “See you understand Dean.”
        Like I birthed him, baybay! Lol, I’m in love with all that he is ;D

        “I am seeing our Dean in a different light already. Thanks Virile for turning me over to the light!”
        Any day I can help someone understand the wonder that is Dean Winchester is a good day lmao.

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    2. “I never had a problem with Dean loving women. It’s actually a trait I absolutely love about him, and a reason I’m constantly annoyed with those who want to turn him into a monk or force him into a same-sex relationship in canon. He loves posse. He’s a posse magnet. Make that into a t-shirt and deal with it.”
      THIS^

      Liked by 1 person

    3. As Dean questions Castiel about his use of protection during sex with April in s9, one might assume that Dean uses protection in these circumstances as well. He knows all to well the consequences. Even in “Spice Girls” he admits to using protection, even if there was an accident and he impregnated an Amazon. He is responsible. It is much a part of his character has his base desires for the pleasures. Food/ sex pleasure areas of the brain. His ferocity follow through in all of his actions and decisions. Sure he taught Sammy to be careful as well. but well Sammy kind of goes dark sometimes. The show does have a moral compass and social statements are often part of the subtext.

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      1. “He is responsible. It is much a part of his character has his base desires for the pleasures. Food/ sex pleasure areas of the brain. His ferocity follow through in all of his actions and decisions. ”

        Exactly, Debbab. He’s responsible and he wouldn’t turn tail and ditch his responsabilies if something happened. The way he reacted to the possibility of Ben being his child proved that.

        What I love about his love for women is that’s it’s integral to his character. There’s something open and generous about Dean. He embraces life and doesn’t denies himself the simple pleasures. I’m touched at the way this rugged, bruised and battered hunter reacts to finding a nicely wrapped pair of chocolate bars on his pillow. He knows pain all too well but he’s not bitter. He wants to laugh, have fun and share the love. Let him. God know he deserves a little tenderness.

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  2. I think his problem rises from the fact that he hasn’t had healthy female interaction. It’s always been sex. He hasn’t had stable, healthy female relationships either. Some part of him is probably majorly stuck and underdeveloped psychologically which is why he gets so excited about going to strip clubs or picking up pretty girls at the bar to take home later at night. With Demon!Dean, it was there as well except he was at a whole new level with it. It’s surprising how much Dean wants to feel but doesn’t. Based on psychology, it could be because of Mary dying very early on and then the way John brought them up. His Oedipul complex hasn’t resolved properly maybe and that’s why he’s always ‘womanizing’ or finding a new girl to sleep with.

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    1. You are spot on with this Susannah as I wondered deep down if it had something to do with his mother dying young, that he needs to find some sort of comfort from a woman that he didn’t ever find with his mum. John could also have something to do with it too being very driven not letting the boys have any or much down time to explore life. No wonder Dean strays, and wants a piece of the action. Its been an interesting topic to explore….

      B xxx

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    2. And his job prevents him from sustaining a relationship and resolving his attachment issue. Mary gave him pie. Dean searches for that perfect piece of pie. You can figure out the desire/fulfillment equation.

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  3. Dean is a healthy 30 something year old male who enjoys recreational, non-relation based sex. His partners are above the age of consent and do give consent. His job has taught him that life is fleeting and that you catch the good time when you can. He does not bed every female that walks by, but he does take a look. The job always comes first. He is capable of a faithful relationship as seen by his tossing the waitress’s number when he is with Lisa- unavailable guys are more attractive he says. His job prevents him from sustaining a one-one relationship. Dean goes into everything he does fully-hunting, fixing Baby, caring for Sam, and when he is with a lady he seems to give it his all as well.
    This is how Kripke infused the character with dimension. Dean has an emotional base that sometimes is counter the hero archtype- we see that tear. He finds a release in casual sex which in modern society is part of the make-up of the “super hero” or are superheros supposed to be sexless like a Ken doll? He does resort to porn at times and there have been references to auto-erotic situations, but being a young, healthy, male with an attractive over all appearance, he finds that human connection no matter how brief it may be.
    As Demondean, he continued what Dean would do but had none of the humanity towards his partner as seen by his treatment of her in that episode s 10. She thought he was a good guy and great in bed with that thing he does with that thing, but she calls him on his being not so nice-again that is the demondean. As a human, he seems more caring about his partners and can turn sex down- Jo- he was afraid of Ellen- even though the attraction is there. His proximity to Jo on her first hunt arouses his sexuality”I should have cleaned my pipes” but he refrains.
    Is he looking for that release, that human connection? Freud may say it has something to do with his mother- that conversation is for another day.
    Dean is drawn as a multi-dimensional character with flaws and if some would like to use “womanizer” for me it has a negative cast. He likes women. He likes sex- review his description in the therapy group. Is he a mysogenist?- not in my opinion. He is fleshed out as a character. Now for those who ship Destiel- or Crowdean, that is another article to be written- it is always about the subtext.

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  4. I don’t think Dean is a womanizer. I think he just likes women and sex. It’s always consensual and a lot of the time the women flirt with him. He also doesn’t always say yes..remember the episode on the ranch where they want to gank a Hellhound and the pretty gal that takes care of the horses comes on to him. The hunt always comes first. I also think he does one night stands because he knows he can’t keep anyone he loves safe. Its hard enough keeping himself and Sam safe. I think at heart he is a romantic, as we saw in About A Boy.

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    1. Dean learned at an early age, that having friends, a normal relationship does not work. He tried with Lisa and his work followed him home. His “apple pie life’ is not possible, so he eats pie, and finds his release as he goes- it is always consensual. That is the difference between modern heros and those of the 1950’s and before on television and in movies. No judgement on the morality of the character; he is well drawn by the writers. Would you want him less dimensional? And to objectify Dean- well it seems to have caught more than a few female eyes.

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