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.