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He's dumb, he's really dumb that's all I'll say but the thing the story is making clear is that there's more than one factors that affects MC's relationship with the other characters and despite all the loops. Taewon is the only one he actually had consistent genuine connection with in regards to the fact that he's the only one he actually liked romantically. (I only saying this because of the prompt he got that he finally learned how to make genuine relationships.)
MC is by far a perfect person, he's emotionally driven with a high moral ground and extreme loyalty to the people he cares about but he's also as vindictive as he is kind. He's not a two sided character made to test the water of character troupes and dynamics which is why I love how this series really builds on each character's connection which says a lot because I don't mind the love quadrangle they're having on right now. It's incredibly hard to find a harem BL story that gives actual justice to the writing like this one does.
That's why I actually like Taewon's character, he's subjected to his own character arcs too and we had glimpse of that with his relationship with Woojon in the future from the side chapters on the end of season 1. He has his own flaws, growths and values but at the end of it all the choices he makes were done out of naivety and ego which comes to bite back at him later on. Anyway, I'm pleasantly surprised I love their interactions and I can't wait to see how this story goes.