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It's been a long time since I read it to be fair, but it's stuck with me i think because at the time I struggled to understand Gene's feelings about Finny, but I get it more now. They came immediately to mind as a parallel to the Toshi/Enji dynamic.

If Enji is very good at one thing, it's making himself suffer needlessly u_u Toshi's kindness would just make him hate himself More i fear.

Such a good question re: Gran Torino ! I headcanon that he is someone who struggles with emotional vulnerability, both his own and others. We know by the time of canon he loves Toshi, but i don't think he's ever Said it aloud. So while i think he might recognize that Enji's motives in getting closer to Toshi are less genuine than Toshi believes them to be, he wouldn't say anything direct to Toshi about it because in his mind he is Toshi's teacher and mentor and it's not his place to involve himself in Toshi's personal matters if it isn't affecting his training. He'll regret this decision later when the breakup happens because he saw it coming but didn't warn Toshi, not wanting to disillusion him about his friend.

Nana's would be the shoulder Toshi cries on, if he allows himself to cry about it. It may be that he forces a smile for her and she, not wanting to pry, doesn't ask him about it. But she learns what happened from Gran Torino and tries to console Toshi subtly. Perhaps telling him something along the lines of "Sometimes a person is so at odds with themself, everyone else looks like an enemy, too. And there's nothing anyone can do about it until they fix what's broken in them."

And she gives him a pointed look, inviting him to talk abt it if he wants to. Maybe some of this gets through to Toshi. But his martyr complex might make it so he internalizes Enji's problems as his own fault too much to hear it, not until he's older. Maybe learning about Enji's abuse of his family is the thing that finally convinces Toshi he isn't to blame.

I could def see Enji trying to "best" Toshi sexually. But maybe as they continue fooling around he realizes he's developing real feelings, which in his eyes is just another win for Toshi, another reason to look down on him, another reason for Enji to hate himself. Because he can't even resent Toshi the right way, had to go and become his friend and then This, whatever it is, doesn't want to call it dating because Toshi doesn't act any differently toward him than he ever did so he assumes it doesn't mean anything to him (and of course it does, but Toshi hasn't said anything because he didn't think Enji would want that). He can't help himself because Toshi is just too damn lovable, and perhaps it's That that pushes Enji to the breaking point.

My first intuition for endmight as classmates at UA is that they would be similar to Gene and Finny from A Separate Peace. Idk if you've read it (sometimes required reading in US public schools), but for anyone who hasn't, the book is about students at an all boys private school during WWII. The main character Gene excels at academics, but envies and admires his best friend Finny's effortless charm, courage, and athleticism. Eventually that envy begins to turn into resentment, with some potential homoerotic undertones depending on your intepretation. But the resentment eventually leads Gene to hurt Finny and causes the dissolution of their friendship.

As we know in canon Enji has been envious of Toshi's strength from afar for the majority of his life, and i think that would be strengthened if they had actual interpersonal contact before becoming pros. Bc Toshi is such a genuinely kind person, Enji would Know his resentment is unfounded and entirely his own problem. I think he wouldn't be able to help himself but stick close to Toshi as both a form of self punishment and to try to work his resentment out by force. But because he can't actually deal with his emotions in a healthy way, he eventually has to take it out on Toshi, who up to that point had thought they were actually friends, or close to friends anyway.

As far as bkdk comparisons, i think Enji suffers from a similar sense of inferiority as Bakugo bc he knows Toshi is a better person than him, but rather than turning it outward from the onset like Bakugo does when he bullies Izuku, Enji bottles it up until it explodes out of him in the messiest friend breakup ever. I think the worst part of it all is Enji wouldn't even actually be able to hurt Toshi physically, but knowing he's hurting him emotionally would satisfy something in him anyway. Like internally the thought is "I may not be able to ever surpass you, but I at least can still hurt you." Finally, Toshi doesn't seem so untouchable.

As for Toshi, I think he would like Enji's dedication to becoming stronger, mistaking it as simply a desire to be the best hero he can be. He'd see Enji's frustration with his limitations as something he can help him overcome by getting closer to him and encouraging him, but privately Enji always receives it as Toshi mocking him, even if he Knows Toshi isn't that kind if person. But just as Toshi thinks he's breaking through Enji's shell, the blowout happens.

We've seen how Toshi tries to brush past it when bad things happen to him, and I think he would similarly try to act like everything's fine afterward. But there'd be a noticeable difference in him in that he doesn't engage as enthusiastically with his classmates, and doesn't try to get close with any of them anymore. As for Enji, they don't speak unless necessary.

Ahh this wasn't very romantic, i'm sorry! I unfortunately feel that, whatever feelings of attraction they might have for each other would be occluded by Enji's problems before they ever get to a point where they can acknowledge it. But for sure Enji having romantic feelings for Toshi would only make his spiralling self-image worse, because he can't reconcile feeling that towards him when he also envies and resents him, and is also confused about whether he really wants to Be Toshi or to Have him. Maybe Toshi knows how he feels already but is waiting for Enji to get to a place where he can accept it. But that day never comes u_u