I should preface that this perspective is formed from the fact that four of the gay or achillean men that I knew in the fandom left around the time of the Epilogues; that wound up being a final straw for them.
It's a topic that we'd discuss from time to time and I felt it could be a valuable perspective to share.
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So, to start off, the main focus point of this whole thing is going to be the characters of:
Dave, Jake, Dirk and Karkat; with minor mentions of other male characters who express homoerotic behaviors.
Dave, I think it's to nobody's surprise, is a brilliantly written bisexual man; but that is due to the fact his bisexuality is a retroactive reading of his earlier behavior. When Hussie started out with this webcomic, I do not believe for a second that there was intent for Dave to be interested in men in any sincere way. I think that was a decision that Hussie made due to interaction with fandom and retroactive perspective on their own authorship.
The "you're so gay" epithets and attacks on masculinity that Dave was prone to in the early comic, later become recontextualized as an internal fear of his own latent attraction, something which culminates in his confrontation with Dirk, where he not only realizes that Dirk and by extension his own guardian, is gay, but that the ascribed "masculine ideals" he perceived were not translated completely.
Dave assumes a degree of irony with what his guardian does and thus, as a defense to his own self, couches all his own interest in that very same irony, for fear that any genuine intrigue would be met with homophobia.
So far, so good.
The problems rise when his relationship with Karkat finally gets a chance to bloom. Dave's bisexuality is only really given breathing space in the last leg of the comic, where his newfound romance with Karkat mostly takes place off screen and is informed to us by external characters and external mediums like twitter and tumblr posts from people close to Hussie. That's not *too* bad, there's nothing wrong with it inherently and I don't particularly mind it, I think it was a nice send off for his arc and a subversion of expectations when it comes to the archetype he filled early on in the comic.
You can make some commentary around the fact that it's frustrating the only (at the time of the comic's ending) canon achillean romance is danced around so hard, with no explicit in universe confirmation, but it's not the end of the world.
Things take a turn for the worse within the Epilogues, though. Their romance is walked back multiple stages and we now find out the most they've managed to do is hold hands, which is fine if it means we're going to get a healthy exploration of their romance which we did not get to see on screen, but it comes at the cost of painting Jade as the invader and falling into a trope that Hussie also utilized with Dirk and Jake, where a woman is coming between them somehow. I don't think it's a particularly fair depiction for Jade and it's an even more awkward depiction of adults, given that Dave had a whole discussion near the end of Homestuck where he was asking Dirk for advice on how to come out to his friends.
It gets even worse when we consider that by the time Dave and Karkat finally kiss, the narrative threshold has been thoroughly taken over by Dirk and he is practically playing dolls and trying to force them into it, which to me as a reader and to my friends at the time, tainted the innocence of their former romance. We get explicit confirmation that Dave has his faculties in check as he shakes off Dirk's narrative forcefulness, but no such moment is granted to Karkat, leaving a sour feeling that the only reason it happened is because Dirk made it happen, which sucks. Male/Male romances in Homestuck seem to now just follow a trend of always being under some form of duress.
Bringing us to the allstar couple of Dirk and Jake.
The background we have on both of these men, before we even meet them, due to internal and external media, is that Bro Strider is an overbearing abusive guardian who relentlessly trained Dave for SBURB because he wanted Dave to be able to survive the lethal game, even at the cost of Dave having a happy childhood, whilst Grandpa Harley was a billionaire gallavanting around the planet learning all he could about the game (and seemingly having a lot of illegitimate children... thanks Hussie.)
The nugget we can draw from these Beta depictions is that Dirk at his core will sacrifice happiness and feelings for the sake of what he considers the greater good and Jake is avoidant of all responsibility, using adventure as a way to ignore any problems he leaves in his wake.
Dirk is a brilliantly written gay man, which when me and my friends first read about him, truly shocked us. I can count on one hand the amount of fictional gay men that I have seen, depicted facing the struggle of internalized homophobia in the way that Dirk experiences it; and that is to say, Dirk isn't disgusted with being gay, but he believes his homosexuality is the original sin that prevents his friend group from experiencing happiness.
He believes that because he is gay, he is screwing up the potential couples in his friend group. If he pursues Jake, he denies Jane the chance at him, since they both like the same man AND he denies Roxy himself, which stings even more when he considers that they are the last two living humans in their Earth. Brilliant. 10/10.
Dirk later discusses the idea that if he could be interested in women, he could give Roxy what she wanted, because he genuinely believes that she deserves it; it's a gut wrenching admission and at the time of reading it, I remember all my friends just feeling for him.
This moment however, arrives after Dirk has already been ghosted relentlessly, lambasted by his own AI assistant and allowed his closest friend to assault him because he loathes himself. Dirk kisses more women on screen than he does his own boyfriend (not that their kiss was not given any gravitas), but I do think it's supposed to be part of an intentional motif with his character; the fact he sacrifices even his own desires for the greater good, but when even the trickster juju doesn't "fix" him, he finally lets his true feelings spill.
And that's about as much as we get with regards to the whole thing. The Epilogues roll around and Dirk morphs into an unrecognizable creep, who winds up doing many fucked up things for god knows what reason.
Jake, on the other hand, fills the role of a "macho" man, which is supposed to highlight the irony that he really isn't any of that. He's sensitive and avoidant and wants to live up to his friends expectations but falls short all the time because he's also selfish and willfully ignorant; a trait which winds up ruining his relationship with Dirk, as they both press the wrong buttons.
Dirk won't *allow* him to be avoidant and Jake worries he'll never be as amazing as people expect, so he'd rather not try, than fail completely, ignoring that these are both effectively the same result. Jake also tends to get sexualized a lot, something which brings him his own discomfort, and is threatened with sexual assault (and later experiences it, but I don't really want to go into that. I don't think that plot point was done well). There's even a callback moment where, much like another Page earlier, he is lifted by a Serket and about to be kissed against his will.
All of that to say, Jake is rather prone to having people be creepy around him, and even though Dirk's convoluted plan to get them to kiss (orchestrated by HAL), is definitely CRAZY, there was never anything beyond that between them that screamed "creepy".
Until of course, the dystopian horror of Trickster Mode, where Jake, fueled by the JuJu, flaunts intense heterosexual desires in Dirk's face and flaunts the idea of them all having babies in some kind of big polyamorous quaouple. It's meant to be this viscerally creepy moment where Dirk is left as the last bastion of rationality, and even he gives in because he's depressed.
And that's where the comic leaves us for their interaction on screen. We get a minor "they might talk" after Dirk and Dave's discussion, where it seems clear Dirk wants to resolve things between them.
And then everything that happens to them and between them in the Epilogues happens, it's too much to list; but I do find it weird that not ONE M/M couple has any kids. Rose and Jade manage to have a secret child that is then ascribed to being Jade's attempt at having a child with Dave. John and Roxy have a child. Rose and Kanaya adopt a child and Jane forces a child with Jake.
This is where I'll segway in to discussing Rufioh and Horuss. The Dancestors were never all meant to be serious characters, and at the time of the story, they were parodies of random Archetypes, but the relationship between Rufioh and Horuss was meant to be a reflection of Jake and Dirk, with Damara acting as a version of Jane. A horse obsessed "creepy" guy who builds machines that is so overbearing he won't take the hint that the shy guy that EVERYONE has the hots for doesn't really want him anymore. I'm not entirely sure if Hussie was making that as an intentional commentary of their relationship or if it was supposed to be a parody of the way the fandom TALKED about their relationship.
Given that there's been endless shipping wars between JakeJane shippers and DirkJake shippers, as well as wars between DaveJade shippers and DaveKat shippers, it's not lost on me that it's easy romance drama to place the key women (namely Jane and Jade here) as the antagonist to these achillean romances, but it's kind of exhausting that it happens twice, even if in different ways.
I think I lost my train of thought here, but my final point is that there's not really any M/M romance in Homestuck now that don't involve some creepy element of coercion to them, which isn't exactly fun to read when gay men are treated as sexual predators IRL.
I just hope things can be different going forward, or things can be changed.
