If he has internalized homophobia then why he has no problem telling Dave he used to date a guy? Like, as you said, he cares about his reputation, and we know he really wanted Dave to like him, so that prolly means he was quite careful with what he could or couldn't say in front of him, specifically after he discovered that Bro abused him. So what I'm trying to say, if he cared about being gay, I think he would have avoided telling him he dated Jake? Or at least give it a second thought? I don't see what's the problem with Dirk being against labels, he seems that type of person, he prolly thinks that makes him more intellectual or some stupid thing like that
Hmmm thats not exactly what I said. I don't think Dirk has internalized homophobia so much as <he's afraid of the outside reception to the fact that he's gay, and how people will perceive him based on it>. Dirk knows that he's gay. We know Dirk is aware of that since he was at least 13, because he's already throwing undeniably romantic advances at Jake by then to test the waters. Dirk isn't in cutesy denial about anything here, he doesn't have the time or luxury for that. His problem is more that once you state 'Yes I Am Gay' as a definition of your character, that comes with a Lot of historical baggage and expectations- and from dirk's perspective, both the expectations and historical baggage are something so incredibly divorced from his reality in a future where no human society exists that he's waaaayyyyyy too careful of making that association. It could potentially bust the image he's trying to project.
Again, Dirk's thing is performance. Esp the performance of masculinity. He is the one homestuck character that truly, genuinely, wholeheartedly cares about putting up an image of what it means To Be Masc. He does this because he likes it. He's not forced to do it, he's not under societal pressure to do it, he's not whinning about how much he hates it, he's not doing it at gunpoint; this is a set of parameters he came up with for himself, even in complete isolation. They are a statement and holy boypledge he's making.
He thinks it is Very Cool, and he would like it if you thought it was Very Cool Too (especially if that transmits an image of how strong and reliable he "totally" is). And, again, when you think about our early 2000-10's context of GAYNESS, because homestuck is an extremely time-bound comic, the image "being gay" summons is... really not the one I described above. We're talking about gay men being stereotyped as catty & cowardly & effeminate, about the constant punchlines around 'useless fairies' (a term that was used to refer specifically *to* feminine, submissive, oft gender-transgressive gays ) not incidentally, Dirk's godtier is revealed to him in-comic through a drawing that depicts him as a fairy. He's immediately put off by it. Dirk and Jake's godtiers were called Fagtiers by more than a portion of the fandom. Relics of this are still high up on google images if you search for pictures of their godtiers, lol. Essentially, to admit to his gayness openly and broadly in that timeframe is to be stereotyped as something he doesn't entirely identify as, in an environment that is far from welcoming.
I am pretty open about reading Dirk as a trans man, and what I think is happening here is that together with Roxy's constant insinuations that Dirk Should Have Her Babies, Dirk is ultimately afraid that his claim to being a homosexual paints him as innately womanly. He either gets to be a man or he gets to love men. There's no middleground, or else these social features will cancel eachother out like pemdas. What we see in Homestuck is his haphazard attempt to keep both things intact. His courtship of Jake is only allowed if it is strictly masculine, if it seems like he has a semblance of control, if it looks like they are both just Dudes being Bros throwing it down like Fellow Action Men. This is harmful for Dirk and gives him extreme emotional constipation; not to speak of how tiring it is for Jake to try to keep up with this months-long improv game of Xtreme Axe Bodyspray Marathon when they could just... date. Jake really wouldn't mind if they decided to paint each other's nails or have stereotypical sleepovers or just chill out and have fun like Jane and Roxy are obviously doing. Jake would be fine with being soft so long as he's not being made fun of. But Dirk struggles with letting any sign of dangerous sensitivity show under the assumption that it will be read as a weakness, an inadmissible vulnerability in his set of armor.
Which becomes all the more relevant once you note that when Dirk's trying to convince Dave that he's not a threat and certainly not a monster, one of the first things he admits to is "I like men."
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