Spoilers ahead, but you're likely playing this first before looking at the comments.
Theme: Not quite present here. Expansion of friend group? But then they're pushed aside narratively?
Story: You were authentically hitting up beats that I see in manga, so that was fun. As soon as they were in the locker room for the side story, I knew exactly what tropes you were pulling, having seen it so many times before.
I liked the explanation for why Akuma was into Haruto, but I kind of wish we saw that ourselves. The Haruto on screen was very boyfail, and Akuma's explanation gives him more depth that I feel like we're lacking. We're getting that sort of archetype of the harem protagonist who doesn't have much going for them but builds up a harem nonetheless (I don't have to name names, you can throw a rock at most mangas and find an example). There was too much self-deprecation, to make the interest feel earned for me. Haruto says he's not worth being interested in so much that I believed him, even if he is a cutie patootie.
Honestly, I was kinda feeling the romantic tension between Udon and the Dalmatian, and was ready for the narrative to focus on them instead. You did a very archetypical bully with heart of gold who people make more assumptions about but he still is tough, and I cant' help but think that this is relatively in the same conversation as Worst Dating Sim, my beloved.
The boss of the meat store knowing the bully has a heart of gold? Of course. Treating him for the date? Of course. Protag likes gaming meaning arcade? Of course! Stalks him at the con? Oh boy.
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Story Aside: Hatsune Miku? Minus a quadrillion point, I don't make the rules /s
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Presentation: Love your music usage--felt very anime, upbeat, preppy, but that made the brief moments were there were no music stand out. Also one track felt like elevator music which was an interesting choice.
I kinda wish they were wearing sailor outfits(the gakuran), as those are really iconic for delinquents in iconic anime/manga throughout the years (Jotaro, Kuwabara, Josuke, Yusuke, whatever is happening in Tokyo Revengers that I didn't read). Even in Beezelbub, some of the chars still wear the outfits.
Bunny? Slay. Diva. Icon. Queen. Mother.
The background filter adds consistency to your fun black and white style (and allows for the color finish), but it muddied the backgrounds a bit. I wonder if more time could have been spent in altering the backgrounds to ensure that they didn't come out so muddy. Or maybe if you did brief sketch ones instead, as those would also be black and white and fit in to the themes? Idk.
Akuma's pose speaks to the stiffness he carries, but I almost wish his arms moved at least a little. He's so tall compared to the rest of the cast-- I had to keep going back to look for the expressions because his face was my only cue and he's the tallest thing on screen. Far away from the text.
Creativity: I like your usage of black and white (which is perhaps due to the time constraint) and making it into a stylistic choice that brings it closer to some of your inspiration's source material... manga!
The narrative beats felt very expected and derived from that very same inspo though, and I think the delinquent uniforms could have stood to be the same level of baseline expressive as the bunny with her tie and mask.
Overall Thoughts: You hit the mark on making your own take of this manga trope, and I can see why everyone is flocking to it. It's fun and cute.
I just wanted more derivation from these tropes and beats, because I already read too much manga for my own good. I needed more than the one-shot chapter. I needed this to get to serialization's changes.
Your art style really meshed with the story you wanted to tell, and I can see why you're gonna be one of the top rankers of this game jam, and it's not undeserved. Good job! And hopefully your other works will continue to get more attention now as well!