The artwork wasn't all that bad. I think it's just the design of his jacket that kinda sucked.
And it wouldn't be the first jacket in the world that makes people look fat. But someone who cosplays would presumably be better at fashion choices than that. I've met many cosplayers, and they tend to add a dash of that style into their everyday outfits.
(Like if you like Izaya, maybe use his iconic jacket, which is still somewhat normal, or add cuter stuff if you like cuter characters and whatnot.
I'll admit I am not expert on average people since I don't so much cosplay as changing my normal everyday wardrobe to fit my favorite character. lol)
You hinted that you can get married in what it said about the game, soooooo.... lol
Any chance he has a cat-loving brother instead? xD
Honestly tho; I think that if you kept developing the game a bit more, it could become a really great game.
I know there is many games entered into a Jam with word limits, where the creator keeps improving the game after the competition is over.
And some of those games turn into great, full-length games.
Your game is like the beginning of a really sweet romance game.
I normally am all for choices, but when it is all chat and no action, it can get a bit tedious with so many of them.
(Although I'd love more ending choices. But I see why a short game like yours only have 3.)
If you streamline them a little bit, and add more actual dates afterwards, you have a good recipe for success.
Because both the art and the writing was pretty good.