Dean Winchester, I would argue, is one character that’s still currently on television who’s sexuality is most often debated. Yes, fanfiction has shown us that no one’s sexuality is safe, Sam Winchester is also often paired with men in the fandom, but there is a difference in how the fans talk about Sam and Dean as far as sexuality goes. Fans write many essays analyzing the characters motivations, inner demons, and yes even, sexuality. The difference here is that there are numerous essays about Dean being possibly bisexual. Dean’s sexuality, as far as the fans are concerned, is up for debate. Sam’s is not. There is clearly something about this character that makes everyone questioned his sexuality. So let’s take a look at Dean Winchester.
There are a lot of essays analyzing Dean’s sexuality, but not so many (if any) do the same for Sam, and this is despite all of the Sam/Dean fanfiction out there. Oh, there are essays about Sam/Dean and homoerotic subtext in the show. Even essays about how they are in a relationship, but I have never seen a individual essays just about Sam’s sexuality. It’s always about Dean.
This is interesting because if we must put hetero-normative or cis-normative features on to characters then Dean comes off as the more stereotypically masculine one. Dean likes classic rock, wears leather, knows all about cars, he sleeps with and objectifies countless women. Dean seems to live by a code that dictates his behavior as a man that is seemingly learned from his father. Dean constantly cites these rules (one day I should make a list of them all) often as a way to put Sam down for whatever “girly” behavior Sam is engaging in at the present. Sam, in the show, is portrayed as the more geeky/feminine one. Sam has a sensitive side, Sam is not as aggressive (in the earlier seasons) as Dean, Sam looks down on Dean for sleeping around and objectifying women. In the episode “Tall Tales” when Sam and Dean are recounting their interactions with the Trickster to Bobby their perceptions of each other come through depending on who is telling the story. Sam shows Dean as being a kin to a stupid drunken chauvinistic frat boy, while Dean portrays Sam as being a nagging effeminate little bitch. It is perhaps because Sam seems more in touch with his so-called feminine side that is sexuality is never questioned. Fans see Sam as straight and accepting of his feminine side at the same time, whereas Dean, being stereotypically masculine and disliking anything stereotypically feminine must somehow be repressing homosexual tendencies.
Let me first just say how much I hate this perception of the characters. The idea that a more gentle caring character like Sam is feminine, and a more aggressive violent character like Dean is masculine really puts them into confined gender roles that have been dictated through patriarchal structures. A further understanding that if Dean is not at least a little stereotypically feminine then he is repressing his “true self” is just as absurd and sexist to me. Now before everyone gets mad at me it is just as sexist and heterosexist to assume that Dean isn’t gay or bisexual or whatever, because he is stereotypically masculine. So for the sake of this essay let’s not assume a character’s sexuality based on whether they seem masculine or feminine—this has nothing to do with sexuality. I have known very feminine straight men and very masculine gay men and vice versa, furthermore these ideas of what is more feminine or masculine was invent by a patriarchal society to begin with. So let’s forget about it.
Next lets discuss sexual kinks. To all the heterosexuals out there, you of course only have very boring missionary position style sex right? You don’t? That’s because sexual kinks also have nothing to do with sexuality. Some of the evidence cited to show that Dean isn’t straight comes from the episode “The End.” Where Dean reveals that one woman he was with asked him to wear her silky pink panties. Not only does Dean admit to doing this, but he also admits that he enjoyed it. Many fans have cited this as evidence toward Dean not being straight. When in truth more straight men like to wear women’s clothes than gay men do. Furthermore, sexual kinks do not indicate sexual preferences. Even if this girl had asked Dean if she could try using a dildo on him and he said he enjoyed it this still wouldn’t mean that Dean was attracted to men it just means he enjoys physical stimuli. Now some people do use Dean’s canon pantie kink as indication that Dean is more pansexual or at least extremely open when it comes to sex. Basically, the argument goes that Dean likes sex so much that he has no objection to trying any kinks, fetishes, or genders as long as he gets pleasure out of it. While this could be true there is no evidence for it. The pantie kink is the only thing that Dean as specifically mentioned and does not indicate that he enjoys any other kinds of kinks. Furthermore, having multiple kinks does not mean someone also enjoys multiple genders. A person can be straight or gay, and enjoy any number of kinks.
So now that we rolled out gender roles and kinks, let’s look at the actual show. First, there is the idea that Sam and Dean have a sexual relationship. This does not make Dean gay. Incest is different than being homosexual. If two characters are engaging in incest it shows that there is some deep trauma that happen to the characters that caused them to be that way. Then we have Dean and Cas. Most of the evidence for this pairing is fans looking into the characters interactions with each other. Yes, Dean and Cas are very close. They have a profound bond and are extremely good friends, and they have both gone through hell for each other. They could be in love. They could also be just good friends. Right now, as far as the show goes there is only evidence of them being friends. When analyzing Cas’s sexuality in a previous post I did admit that Cas is probably not straight simply because of his nature as an angel. Sexuality and gender is not something Cas would understand in the same way we do. So it is conceivable that Castiel is maybe in love with Dean. But Dean has in the show has always dated and been with women. Is there any evidence that Dean could lean another way?
Well most instances where people claim evidence of Dean’s sexuality can be easily dismissed or explained away. But there is one instance where explanations are few and far between “Changing Channels.” “Changing Channels,” is the only episode I feel I could point and say, “Dean’s attracted to that guy.” In the episode, it’s revealed that Dean likes the TV show Dr. Sexy and likes Dr. Sexy himself more than a little. When Dean meets the fake Dr. Sexy that the Trickster created he blushes, ducks his head, shuffles his feet, and overall acts like a boy with a crush. When he realizes that it’s not Dr. Sexy he actually states why he thinks Dr. Sexy is well, sexy. There is clear attraction here. One that mirrors the episode “Hollywood Babylon” were Dean and Sam work a case on a Hollywood set. Dean’s attraction to the actress on set is almost identical to the attraction he has for Dr. Sexy.
So is Dean straight, gay, bisexual, other? Canonically I’d say he’s straight, but much like Willow in Buffy the Vampire Slayer I think should the writers decide to write him as bisexual there is certainly enough subtext and even some text that would make it realistic.
Some other essays about Dean’s sexuality that or worth reading. WARNING: Some are definitely bias toward one pairing or another.
“Well, You Are Kind Of Butch”: The Bisexuality of Dean Winchester
Lady Geek Girl and Friends 
“Well most instances where people claim evidence of Dean’s sexuality can be easily dismissed or explained away.”
What’s the explanation for Dean checking out the guy in Time After Time? What about Sex and Violence where Sam and Bobby are completely unsurprised by Dean’s siren being a guy? There’s a reason Sam isn’t the one that’s speculated about, and it’s not just cause he’s the one that overcompensates (But I mean really “I’m a posse magnet. I’m gonna put that on a t-shirt” “I was busy having sex. With women.” Who says things like that? Ridiculous.)
Thank you for asking this question. I thought about talking about some of evidenced you mentioned and explaining why I don’t see it as concrete evidence more throughly, but I could write a book about Dean Winchester and sexuality so I limited myself to simply saying that I felt most evidence could be dismissed or explained, other than the Dr. Sexy incident. But allow me to take some time here to explain my reasons with some of the other evidence.
Let me first say that if this were a court case incidents like “Time After Time,” or Dean and Cas’ often passionate staring contests would be largely circumstantial evidence. And while I love the Dean/Cas pairing I tried to turn off my fan girl brain and just look at hard concrete evidence.
The instant were Dean seems to check out a guy in “Time After Time” happens really fast. I didn’t even realize it happened until I saw a gif of it on my Tumblr dashboard. I think it’s interesting, but I don’t consider it hard evidence, one because of the brevity of it (I felt I couldn’t effectively analyze a scene that short), and two because there could be any number of reasons Dean looks at that guy. Just because he stares at him instead of the girl doesn’t mean necessarily that he is checking him out.
“Sex and Violence” I don’t see as evidence at all, because the siren wasn’t trying to seduce Dean with sex or attraction, but became the brother Dean always wanted. That has everything to do with familial love and nothing to do with sexual or romantic love. Sam obviously wasn’t surprised as the siren explained to him everything that was going on before controlling him too. As for Bobby he sees the siren take the form of a man and BOTH Sam and Dean are under it’s thrall. So if Bobby’s not surprised by this form he could not be surprised about either or them. Or he could guess that the siren used Sam and Dean’s brotherly relationship against them.
As for these quotes: “I’m a posse magnet. I’m gonna put that on a t-shirt” “I was busy having sex. With women.” Who talks like that? Almost all of my heterosexual male friends when they are joking around with each other. Could this be Dean overcompensating, yeah, but it could also just be him joking around with Sam.
I hope that explains my line of thinking. Again, this is all my opinion, and yet again, I do think that there is enough evidence (both hard and circumstantial) that if the writers decided to write Dean as a bisexual character they could do it and it wouldn’t be out of character, but right now they are definitely trying to write him as a straight character.
Sorry, for the long reply. I hope I answered your questions effectively and thank you for commenting.
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I am not deep in this topic and didn’t learn about Destiel until I had watched several seasons. But early on in my perception Dean had a bisexual tone/facet. One reason I think was that I always felt that he didn’t feel as much at ease with women as he does with men. (Benny comes often to my mind when I think about that.) But then Dean isn’t the most relaxed character anyways and no female character survives long enough (or in Lisa’s case has enough airtime) in this series to make/to really show the building of a closer relationship (be it friendship, colleagues or lovers) possible, so . . .
Another thought I had about this is besides seeing more queer characters in TV shows I would also like to see more friendships/other relationsships between men where on the one side tenderness in general and on the other a certain bodybased affection is shown. I don’t know how it is in the U.S. but in Europe women showing affection to their female friends through hugging, walking arm in arm etc. is much more accepted than the same behaviour between male friends.
That was it from my side.
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If you haven’t noticed, there are a lot of things that Dean does that are pretty feminine, he likes romantic TV shows like the fictional “Dr. sexy”, he also listens to pop and romantic music at times, I mean there are a lot of things in his actions that imply effeminate traits.
I totally agree with you here. Dean has never really struck me as being blatantly bisexual. I’d be fine if he was, and I don’t think it would be a stretch if the writers took his character in that direction. It kind of annoys me when people get into wars over the sexuality of Dean Winchester….I mean, believe what you want but at the end of the day, we love him regardless.
I think you’re missing the point a little. It doesn’t matter whether or not those things mean someone is queer in real life, because this is not real life- this is a fictional text, where the writers make deliberate decisions as to how to characterise someone.
So, I agree that the panty kink thing is actually something that is more of a straight dude thing. In fact, it is *definitely* a straight dude thing in the kinky community- feminisation (forced or otherwise) really only has an impact on straight men, thanks to our cis-normative and heteronormative culture. However, it is an accepted queer-coding trope in fiction, regardless of how accurate that may be in real life.
Additionally, while there *shouldn’t* be a link to the way one performs gender and their sexuality (trust me, as a very femme gay woman, I understand this well!), there nevertheless is- both fictionally and in our world. Hyper-masculine overcompensation to cover up queerness is a thing that happens. That writers have then made it into a trope is not surprising.
Basically, I’m saying that the writers of Supernatural have made deliberate decisions to subtextually code Dean as bi- to ignore all of the tropes (and there are too many to count!) that have been placed into the text is wilful blindness. Of course; it is also deliberate that everything is subtextual and therefore deniable- they want to maintain as wide a base as possible, and wilfully blind straights do make up a hefty portion of that base.
So, is Dean bi? Canonically, no. And subtextually- absolutely, yes! Both of those things are true and deliberate. And, is pretty much the textbook definition of queer-baiting.
And then there’s also the classic argument that text is merely what we interpret of it- so while your Dean may not be bisexual, mine definitely is!
And, I’m sorry that I have the benefit of an extra 5 years of blatant queer-coding, lol. The Dean/Crowley Summer of Love hadn’t even happened when you wrote this post- so the tropes and subtext only got ever more blatant in the five years since. And continue to this day- yesterday’s episode contained very obvious lines. I mean- “I rubbed off all over you”? Really?