Disclaimer: Man, I need a hobby. I read a word-vomit post, pondered some meta, put my thinking cap on, and whipped this out. Can I apologise in advance for the buckets of crazy? I credit those who need to be credited at the end. Okay. Go forth.
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It’s no secret that Dean Winchester—hunter, brother to Sam, the archangel Michael’s vessel for the apocalypse on earth—is a ladies’ man. It’s as much a part of him as his green eyes and his freckles and his astounding lack of self-worth. Cassie, Carmen, Anna, his Amazonian baby mama; Dean has wooed a myriad of women on- and off-screen. But what many people (who aren't in the fandom, at least) don’t realise—what, in fact, Dean may not have fully embraced himself—is that Dean Winchester is bisexual.
Back in the halcyon days of the pre-apocalypse seasons, creator Eric Kripke acknowledged that Sam and Dean were named after Sal Paradise and Dean Moriarty, the road-tripping friends of Jack Kerouac’s On The Road. Moriarty, Dean Winchester’s namesake, has given him more than just his forename: both are witty, charming, fast-talking con men and notorious womanisers. In the original scroll of On The Road, Dean Moriarty’s name is Neal Cassidy. Neal—beat generation hero, inspiration for characters in novels by Kerouac, Hunter S. Thompson and Ken Kesey—was married twice, and had an on-again off-again sexual relationship with beat poet Allen Ginsberg that spanned two decades. Yup. Dean Winchester is based on and named after a character who was based on (and almost named after) a bisexual man. Coincidence. Maybe.
(Fun fact: the naming of Sam and Dean and On The Road’s influence on Kripke is revisited in Swan Song [5.22]. In Chuck’s narration, he says that the first owner of the Impala was a man called Sal Moriarty.)
Arguably, that proves nothing. Not on its own, anyway.
You don't have to look very hard or very deep to see that Dean has weird relationships with other men. This is probably because he had a weird relationship with his father. Read: daddy issues out the wazoo.
In the earlier seasons, Dean idolized his father. He had his dad’s car, his dad’s leather jacket—even his dad’s music taste. He followed his father’s orders without comment and chided Sam for questioning them or for outright rebelling against them. If Dean was consciously modelling himself on anyone, it would be John Winchester: a marine turned mechanic turned hunter. John is a real man’s man, who—when he was around—raised his kids “like warriors” and ruled with an iron fist. He drank, slept with women on cases (Adam Milligan, come on down!), fought in Vietnam and was tough as hell; in short, the stereotypical, macho dude.
But Dean’s upbringing wasn’t your usual tough love stuff, The Tree of Life style. It was less “tough love”—and not exactly “no love”—and more “look after your brother and you might earn some love”. Because Sam has been eclipsing Dean since he was six months old. Dean’s entire life has been about Sam. Since Dean was a little kid his life has been a constant litany of look after your brother, protect Sammy, look after your brother, protect Sammy. When Dean failed at this—when those freaky as hell dementor-like monsters almost suck Sam’s essence out in the flashback in Something Wicked [1.18] because Dean wasn’t vigilant enough, or when Sam ran away for two weeks on Dean’s watch—John punished him, presumably physically (“And when Dad came home…”).
Dean raised Sam. Dean dropped out of high school and got a GED, while Sam went to Stanford on a scholarship. When they start travelling together again at the beginning of season one, it’s about Sam and Sam’s revenge for Jessica. Then they find out Sam has special psychic powers. They finally get John back, but he dies (for Dean, and it eats Dean up from the inside out because he’s not worth that—but that’s a whole ‘nother essay), and his last words to Dean are about Sam. Dean might have to kill Sam, and it’s all he thinks about. Sam gets taken to be part of Azazel’s big scheme. And then Sam dies and Dean has failed again, failed at his most important job—he even says it, as Sam is bleeding all over the ground: “I’m gonna take you care of you. I’ve got you. That’s my job, right? Watch out for my pain-in-the-ass little brother?” So Dean sells his soul for Sam. Dean gets pulled out of Hell by an angel to do God’s work and thinks he might finally be special, but no; Dean finds out he started the apocalypse. His whole life he tried to get John to appreciate him, tried so hard to make something of himself—when it all just came so easily to his brother—but he never could. He couldn’t make John worry about anything other than Sam, he couldn’t make himself worth something, and he was never going to be special.
(He meant something to the angel who pulled him out of Hell, the angel who rebelled for him… but then he found out that that same angel pulled Sam from the pit too—used the same words to tell him about it, even—and Dean realised that no, he wasn’t special, it was all a big misunderstanding. Ouch, that was my heart.)
Since John died in In My Time of Dying [2.01] (i.e. the episode in which shit got real), Dean has been subconsciously searching for men to fill the empty role John left in his life; which is why he’s so great with the guys. Charming. Pally. Constantly trying to please them. Striving for the appreciation he never got from his daddy. Desperately trying to mean something to someone (because yes, Sam loves him, he really does, but Sam never needed Dean in the same way Dean needed Sam).
So Dean is constantly forging relationships with the men around them—feeling them out (oooer) to see if they’ll fit the bill for what he needs: masculine attention, a father figure and, later on in the seasons, a brother figure who needs him back. Which is how Nick the siren manages to work his mojo on him, but I’ll get to that later. And Nick is just another dude in a long line of dudes that Dean’s has connected with on the show, however briefly. Sam is great at convincing distraught mothers and bereaved widows to divulge details; Dean has an instant rapport with the guys they meet. Ranger Rick (“I liked Rick!”), Ronald with the whole laser-eyes theory, Garth, Gordon, Hendricksen (when he finally stops trying to arrest them), Tiny (from prison) and Bobby, to name a few. (Bobby loves both Sam and Dean, but—as he reveals when Dean has been blasted by Veritas in You Can’t Handle The Truth [6.06]—Dean is his favourite.)
Dean was constantly trying to be perfect for his dad, and then he was trying to be perfect for everyone else, and he’s still trying to be this perfect man that he’s raised up on a pedestal, but, the thing is, Dean just isn’t comfortable in that role.
When the show starts, it seems like Dean is going to grow to fill his father’s shoes. He boozes, smokes and does drugs (in subtext, of course—this is The CW we’re talking about, here), and flirts with women constantly—and when he’s not flirting or sleeping with them, he’s referencing flirting or sleeping with them. Real manly, right? Wrong. There’s one Manly Man box that Dean can’t tick: straight. The perfect, masculine dudebro Dean pictures in his head is heterosexual. Not gay. Not bisexual.
(After this essay was originally posted, I got a few messages from people saying that they don't agree that "daddy issues" influence sexuality. That's not what I'm saying at all. I don't think Dean's issues regarding John--and Dean's role in Sam's life--had any bearing on his sexuality, but I do think they potentially changed how Dean reacts/deals with his sexuality.
Look at It's A Terrible Life [4.17]--Dean and Sam are dunked into different lives by the angels in order to prove to Dean that hunting is in his blood, and he'd always find his way back to it. It's not really an alternate universe--the Winchesters have just been given false memories/skills and thrown into an actual office block. Bless.
At some point in the episode, Dean tells Sam that his parents are called Bobby and Ellen. Dean Smith is what Dean could have been if his life was free of hunting--and, more importantly, John's upbringing. And this Dean is... well. He's up at the crack of dawn making fancy frothy coffees and grimacing at rock music in his boring company car. He's sharply dressed--very sharply dressed, all braces and clean lines and colours--and his hair is meticulous. He even looks like he tans. Sam tries to speak to him in the lift and Dean immediately assumes he's being hit on, and tells Sam to "save it for the health club". He eats salads. He doesn't drink beer because he's detoxing. He sits in his office and chats to other dudes about Project Runway. Project Runway!
If we see Dean Smith as a Dean who's entirely devoid of John's influence (and, obviously, the on-the-road, rough hunting lifestyle) we can see that he's almost unrecognisable. He's still Dean--he's sarcastic, he likes hunting, he's more than a little willing to break the rules--but he's also not. He's comfortable with himself, in a way that we haven't seen Dean be before.
So, yeah, I don't think that daddy issues can change your sexuality--but I think they can change your behaviour towards it. Okay. Carry on.)
Dean is extremely insecure about his supposed flaws--as he sees them--and projects them onto his brother. In psychology, this is called The Lady Doth Protest Too Much.
Dean is a typical big brother in that he teases Sam mercilessly (when they’re on speaking terms, and when they’re both alive, and when they’ve not got an imminent apocalypse hanging over their heads or the devil riding shotgun, that is). He’s a typical big brother, except that when it comes to mocking Sam about sex and sexuality, Dean excels at it. There are so many instances of it that collecting them all would probably take watching all of the episodes again, but here are some that stand out, for various reasons.
In Bedtime Stories [3.05], Sam mentions Cinderella and the pumpkin and the mice, and Dean’s reply is, “Dude, could you be more gay? Don’t answer that.” Thanks for your input, man. In Dream A Little Dream of Me [3.10] Sam has a, ahem, dream about Bela (moment of silence of the untimely demise of a fantastic character) and when he wakes up Dean asks him if he was dreaming about Angelina Jolie or “…Brad Pitt?” In Mystery Spot [3.11], Dean’s rummaging in his bag and pulls out a black bra. He turns to Sam and says, “This yours?” Later on they’re arguing and Dean says, “Sam Winchester wears makeup! Sam Winchester cries his way through sex!” In Long-Distance Call [3.14] Dean says, “Pack your panties, Sammy, we’re hitting the road.” In Skin [1.06] he actually says, “Sam likes women’s underwear,” when he thinks Sam isn’t paying attention to him. Funny, that.
The bra and panties lines take on a whole new significance when you think about the fact that, nine-or-so years before the episodes are set, Dean wore a girl’s underwear and enjoyed it: “Rhonda Hurley. We were… nineteen. She made us try on her panties. They were pink and satiny… and you know what? We kind of liked it.” (Ding ding ding! Essay title!) God bless The End [5.04] for being the best Supernatural episode ever. When Dean is uncomfortable with feelings he has—particularly sexual feelings (he has literally never revealed the panties-wearing thing to anyone other than himself)—he projects them onto Sam. When Dean takes the mickey out of Sam for being gay, or girly, or having sex dreams about guys, it probably reveals a hell of a lot more about Dean than it does Sam. The “Sam Winchester cries his way through sex!” comment, in particular, is hilarious—because canonically we know that Dean is the, er, gentler lover. With Cassie and Anna he was all romantic and tender. With Lydia in The Slice Girls [7.13] it’s a little more rambunctious (and with a killer soundtrack)—but Lydia is the one doing the pushing around. On the other hand, we only needed one episode (Heart [2.17]) to see that Sam is a lady in the street but a freak in the bed. Holla.
Most of the time, Dean doesn’t seem to have a problem with homosexuality. The first time it’s really brought up in the show—in that episode we all tend to erase from our minds as soon as the credits roll (Bugs [1.08])—a housing developer mistakes them for a gay couple. Dean points out that they’re brothers, and that’s the end of it. In the next scene, the head of sales approaches them and, again, mistakes them for a couple; rather than go through the “we’re brothers” bit again, Dean just says he’s going to talk to someone else, says, “Okay, honey?” to Sam and pats him on the arse. True, it’s partly to embarrass Sam, but whenever anyone mistakes Sam and Dean for boyfriends, Dean always seems more squicked out by the fact people think he’s gay for his brother—not that people think he’s gay.
In Something Wicked [1.18], when Michael delivers the infamous “two queens” line, Dean never actually gets around to correcting him. (And, man, I’m not a wincest shipper, but that line is delicious.) In Playthings [2.11], they’re offered a king size bed at an inn. Dean says, “Of course, the most troubling question is why do these people assume we’re gay?” Sam, rather than saying, we’re two young, good-looking guys asking for a room together, genius, says, “Well, you are kinda butch. Probably think you’re overcompensating.” The transcript reads DEAN (forcing a laugh) Right. Dean. Honey.
And that’s totally the-lady-doth-protest-too-much-ish. Dean feels like he has to say something to defend his masculinity; Sam doesn’t. Sam just brushes past it. When Hendricksen says he likes seeing them in chains (Jus In Bello [3.12]), Dean calls him a kinky S.O.B. and says they don’t swing that way. When Bobby gives them anti-possession charms in Born Under A Bad Sign [2.14] and says they’ll stop from letting demons “back up in ya,” Dean says it sounds vaguely dirty. We get it, Dean. And, it’s funny, because Dean honestly really doesn’t care. In The Monster At The End of This Book [4.18], Dean and Sam discover fandom and slash fiction; Sam enlightens Dean to what Sam-slash-Dean means, and Dean just says, “They do know we’re brothers, right?” And in A Very Supernatural Christmas [3.08] Dean implies that he and Sam are gay to explain why they need what they need. Dean just puts on his usual smile—Sam alters his behaviour entirely to try and come across as gay (“It was yummy,” bless you, child). In The Great Pumpkin, Sam Winchester [4.07], Dean finds out the witch they're hunting is posing as a cheerleader. He says, "Yeah, well, if you were a six-hundred-year-old hag and you could pick any costume to come back in, wouldn't you go for a hot cheerleader? I would." He gets lost in thought. Sam looks at him strangely. Understandable.
Then there’s the fact that, in his late teens and early twenties and possibly beyond, Dean probably had sex for cash. We know that the Winchesters cheat at pool and poker to get money in bars, but Sam is the only one we actually see doing it; in I Know What You Did Last Summer [4.09], Sam is pretending to be drunk and betting big bucks playing pool, when actually he’s sober as a judge and pretty damn good at it. And, I’m pretty sure, that’s the only time we ever actually see them hustle pool, and we never see them hustle poker. In Bloody Mary [1.05] Dean gets cranky with Sam bribing someone with money that he “earned”. Sam supplies the “playing poker” excuse. At the beginning of Bugs [1.08], Dean walks out of a bar with a wad of cash—and, again, Sam is the one who says “hustling pool”. Dean replies with, “Fun and easy.” We never actually see Dean hustle anything, and—canonically—Sam is the much better poker player.
Think I’m reading too much into things?
“Dean’s a bit of a pool shark and also a bit of a gambler. It doesn’t really show it all the time, but it’s definitely implied that there are poker games and pool matches that they can win some money on. And who knows? Dean’s a promiscuous kind of guy. Who knows how he drums up the funds that they use?” Jensen Ackles, people. Confirming--uh, kind of--what we all suspected: Dean has turned tricks. And do you know how many ladies hang around skeevy bars willing to hand over money to young, good looking dudes? Probably zero. You know how many burly truckers do that? A fair few. “Fun and easy.” Yeah, I’ll bet.
(Disclaimer: I'm not equating bisexuality with promiscuity. As a bisexual person I can tell you that that particular stereotype makes me want to curbstomp a bitch.)
People’s reactions to some of Dean’s lines range from “internalised homophobia!” to “closeted and uncomfortable!” to “straight-up hyper-masculine asshole who’s desperately trying to reassert his manhood!” Okay, maybe those are just my reactions depending on my mood, and maybe they all kind of mean the same thing, whatever. The writers have shown that Sam and Dean treat homosexual victims the same way they would anyone else in Faith [1.12]—one can only assume that, faced with demons and ghosts and horrific monsters on a day-to-day basis, the boys don’t see any facet of humanity more or less worth saving than anyone else. Props.
(Unfortunately, the writers have fallen into the Bury Your Gays trope twice. Arguably, though—in All Hell Breaks Loose pt. I [2.21]—every one of Azazel’s kids die (including Sam) bar one, so it’s not like the writers singled out the lesbian character to bite it. In Ghostfacers [3.13] there’s one gay character, and he dies—but we get the gorgeous, surprisingly moving scene between Ed and Corbett’s death echo (which I’ll talk more about later).)
The three main instances of Dean exhibiting homophobic behaviour that come to mind are in Criss Angel Is A Douchbag [4.12], My Bloody Valentine [5.14] and The Real Ghostbusters [5.09]. In the latter, Dean finds out that the two guys he meets at one of Chuck’s book conventions (who happen to be LARPing him and Sam), are partners. I honestly think the little kind of laugh he comes out with is to cover up the fact that he blatantly just wondered if they role-play in the bedroom—we know from The Monster At The End of This Book [4.18] that Dean is not down with wincest—but he covers it all up with, “Howdy, partners,” which is kind of painfully cute.
In My Bloody Valentine [5.14] Dean is grabbed from behind and shook about by what he discovers is a tubby naked guy. Yeah, the guy’s a cupid and also adorable, but that’s besides the point. Dean is a touchy-feely kind of guy (as much as he "no chick flick moments" his way out of it), but--like most people--he only likes being touched by people he knows, trusts, and who aren't starkers (except, obviously, during sex). Being grabbed by an overly friendly nude man would freak me the fuck out, too, and I drape myself all over people 24/7. Dean's squicky expression probably has more to do with the fact that there’s a big naked dude hugging everyone. (I’ve been at that kind of party. It’s awkward.) Dean gets the same kind of look on his face when the sassy old lady kisses him in Time After Time After Time [7.12]. Sometimes, you just don't want people you're not attracted to touching you in ways that can be construed as sexual. Kanyeshrug.
In Criss Angel Is A Douchebag [4.12], the snarky old magicians (damn it, Barry Bostwick, I love you!) send Dean to an underground BDSM gay club and Dean kind of looks like he’s gonna throw up in his mouth. Three things. One: Dean was taken by surprise. No one expects to be following up a lead on a case and then end up faced with The Chief. Two: yeah, I think Dean is bisexual, but I don’t exactly think he’s been running around fucking guys left, right and centre. Having some huge, leather daddy bear insinuate he’s going to ram you so hard up the back passage you’re going to need a safeword is terrifying. Let’s be honest here. I think we’d all make that face, especially if we were expecting an old magician and got The Chief instead. Three: this one is kind of a stretch, but Dean’s just been carted downstairs into a skeevy basement and is then confronted with some gigantic guy striding out of the fog and saying he’s going to ream him. It’s implied that Dean will be tied down, and he’s gonna need a safeword. To a guy who’s just got out of being tortured in Hell—and don’t get me started on the kind of things they imply throughout the seasons about what actually happened to him down there—that’s about as appealing as an acid bath.
I’m not one to excuse homophobic behaviour, but I really do think some of the things Dean says and does are about him making out he’s super manly because he’s closeted and feels a bit threatened. He teases Sam on occasion, but he’s not malicious, and he’s shown that he treats gay people the same as he treats straight people. There’s even been a study published recently about how homophobic people harbour secret same-sex attractions (cue: collective “duh” from the LGBTQ community). Dean is just one of those not-100% comfortable with their sexuality, allow-me-to-reassert-myself-furiously dudes.
As simply as I can put it: Dean is okay with homosexuality. He's used to people thinking him and Sam are gay (though that freaks him out, a little--especially when people know they're brothers, and still think they're gay) and he even plays gay for cases, on occasion. But he's not 100% okay with himself, and his own orientation. As, arguably, most of this essay is comprised of made-up shit and my reading too much into things, I feel like I can make that statement and I won't get yelled at about it.
Remember that perfect man I mentioned earlier? When the series starts, it does look like that Dean is just gonna be that guy. He boozes, he smokes and does drugs, he sleeps with women, he’s constantly talking about sex, and he takes the piss out of Sam for being “girly”: wanting to talk about emotions (“What do you want me to do, Sam, huh? Sit around all day writing sad poems about how I’m going to die? You know what, I’ve got one. Let’s see, what rhymes with "Shut up, Sam"?”), being soft-spoken and sweet, and knowing things about fairytales (Dean has only seen the porn version because he is a dude! A hunky dude! A badass hunky dude!!!!). Dean is reckless and macho and fulfilling all the stereotypes, whereas Sam is sensitive and calmer and is constantly eye rolling at his brother’s shenanigans.
But you don’t have to stay tuned for very long to see that the first impressions are quickly and frequently subverted. In Dead In The Water [1.03], Dean bonds with a little mute kid called Lucas over them both seeing something really awful happen to a family member. Dean, in fact, bonds with kids frequently. He was Sam’s maternal figure, protecting him and making his dinner and being there for him when his dad was away (and, man, I tried to read some Freudian analysis meta about that, and it went so far over my head it was in outer space). He enjoys wearing women’s underwear—come on, that face—and, physically, is a lot less masculine than his brother: he’s shorter, and rocks those delicate, feminine features. And those freckles. He cries. More than Sam. A lot more than Sam.
Sam, in fact, is the perfect example of the guy Dean is trying hard to be. He’s tall and broad and masculine looking, he’s a tiger in the sack (had to be said), he can be pretty violent, he was rebellious growing up, and he’s described as being similar to John—and, interestingly, that’s implied as a bad thing. And Sam isn’t more sensitive than Dean; he’s just comfortable about showing it, because he’s not having an internalised sexuality crisis every hour of the day. When was the last time Sam told someone he doesn’t swing that way? Precisement. Sam was even named after their grandfather (and Dean was named after their grandmother, welp).
Back the fuck up, I hear you cry. You haven’t actually given us any evidence that Dean is bisexual! He could just be one of those douchebaggy dudebros who’s trying desperately to mask his feminine side!
(This post has been split due it to it being really fucking long. Click here for the rest.)
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