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There are a few things which I feel have defined Dean Winchester’s character in his life. First is his role as caretaker, second is his personal decision to create himself as a foil to Sam, and finally is his need for approval from his father. As you can see, in line with Supernatural’s main theme of “family”, all of these things are familial in nature.
Dean’s primary purpose in his family has always been caretaker. While it can be said that this became his primary purpose after Mary’s death, it’s shown that even before she died, Dean acted to comfort her/act as a buffer between her and John. After her death, he became the only thing between his brother and his increasingly unstable father— and while that in itself would be too much to ask of your average kid, he also was the last line of defense between Sam and monsters. Dean grew up knowing that the consequences of him not being a good enough caretaker was death.
It’s no surprise, then, that even after Sam proved that he could take care of himself, Dean continued to place Sam’s life ahead of his. Dean doesn't put down burdens, he only takes them up. When it turned out that the world was on his shoulders, he wasn't surprised— because all his life, the world had been on his shoulders. Sam was his job. His father was his job. Avenging his mother, saving strangers— everything was his job, because he was there and taking care of people was literally all he knew.
Aside from and as part of acting as Sam’s caretaker, Dean has, consciously or unconsciously, structured himself as Sam’s opposite. At a relatively young age, he decided certain things about both Sam and himself: Sam was smart. Sam was a romantic. Sam was weaker. Sam was more feminine. Sam was ambitious. Dean took these things and defined himself by them— by creating himself as a foil. Sam liked girls, so Dean kissed and told. Sam was smart, Dean dumbed himself down.
These things weren't even necessarily true about Sam, the same as their opposites weren't necessarily true about Dean— but Dean has always had a hard time seeing Sam as a real person, as opposed to a precious thing he had to protect; Dean, in his capacity as A Big Brother has always been ornery. Now, even as he knows these things aren't true, he has a hard time letting go of the picture of himself he has created, along with the picture of Sam he held onto.
Finally, Dean’s relationship with his father has pretty thoroughly screwed up his ideas about masculinity. John was the archetypal Man’s Man— a gruff war veteran, he showed his love entirely through violence and revenge. Incapable of focusing on what he had (Sam & Dean), he dedicated his life, and theirs, to avenging a woman who he didn't fully appreciate while she was alive. Dean comes away from this with a few ideas— first of all, this idea of a “perfect relationship” which is made up of a woman (who must be protected, lest she literally be burned alive) and a man (who has to protect her). This idea is later shaken by realizing that John & Mary’s relationship wasn't perfect, and that she was a hunter— but it still is the foundation of Dean’s ideas about romantic relationships. Secondly, it taught him that love is, first and foremost, something that will hurt you in the end. Love was sacrifice in the Winchester family— love was destructive, love was revenge. Dean had no viable example of a loving relationship in practice— only the aftermath of one gone wrong.
These things all relate to why I believe Dean Winchester is bisexual, and how that would manifest in his personality, specifically post-Season 4.
I’m going to assume that John’s life, if not thoroughly heteronormative, at least appeared to be to Dean. Combine that with Dean’s idea of the perfect romantic relationship and his purposeful decision to be “the masculine brother”, any thoughts or feelings that broke that mold would have been thoroughly repressed.
At least up until a point— and I believe that point would be when he finally realized that he had Too Much On His Plate, or as I like to call it: around Season 4, when he found out that it was “his fault” that the apocalypse was started.
As I talked about, Dean Winchester has set himself up as a caretaker— for Sam, for everyone. Everyone, that is, but himself. It’s when he realizes that he can’t handle everything he’s been handed that he begins to lean— on Sam, but also on Castiel, who has insinuated himself into Dean’s life as a person he can rely on.
Dean has pretty much never had an equal to rely on. Sam has always been his little brother and his priority— he himself has never been anybody’s priority. Strong feelings develop, as they’re wont to do when the dude’s literally the only person who has ever actually believed in you, and Dean honestly does not know how to translate them. His relationships have two settings, 1) family and 2) girls, which is the definition of why he’d have a difficult time having a relationship with a woman that wasn’t fraught with awful.
He calls Castiel his brother, shit goes down, etc. Whether Castiel himself was actually the catalyst or not, I think that from that point on, Dean would have begun to actually struggle with his sexuality, primarily because he had to begin actually examining himself, his own beliefs, what he actually wanted as opposed to what he was supposed to do. He spent time with Lisa, which worked as long as he wasn’t hunting, but hunting is such an integral part of who Dean is that I don’t honestly think he could be with someone incompatible to the lifestyle.
I think that, given Dean’s behavior in the most recent season, purgatory was a turning point. He still tasked himself with protecting Castiel, but there he was completely free from the person he was supposed to be— he was a monster among monsters, and I think he was surprised to find it didn’t bother him. His self-esteem had already been as low as it could get— I think bizarrely, purgatory did him good. He made peace with the part of him that was bloodthirsty, he made friends with a changed monster. He learned that even monsters aren’t bad.
I could go either way as to whether or not Benny and he had any kind of relationship— I think they could have, and it probably would have been good for Dean, but I think canonically he probably broke it off to stick with Sam before it could have gotten anywhere.
Now we’re left at a place where, while still carrying the world on his shoulders, Dean Winchester is more at ease with what he has to do to do it, and I think he’s in a better place, mentally. I think that, were it up to me to write him, I would say he’s currently feeling out the idea of Liking Dudes because he’s back from purgatory and more free than he has been for a while, possibly… ever.
Dean Winchester’s horoscope: it’s an auspicious time to realize that every time he’s told a dude he was “like a brother” those feelings weren’t necessarily super brotherly.
I believe that in the show this would manifest with: growing comfort with LGBT people, being more relaxed in general, casually bring homosexuality up in conversations with Sam, and being flustered around men with potential interest in him-- all things that have been happening.
On that note, I think that to have Dean be confirmed as canonically bisexual would be a good thing for the show-- not for fan reasons, I don't think it matters who he hooks up with, if anyone-- but because it would clarify a lot about his character, bring up interesting issues, and work towards diversifying the show.