Okay so i’ve noticed that Obi is doing his best to hide his past as a criminal in the underground, including his amazing skills but still doesn’t sell himself short.
he clearly missed, but i believe it was on purpose, considering that he pinned a man to the ground by throwing knives at him also:
he shot an arrow a few inches away from Shirayuki’s face, knowing that she was also running up the stairs makes it harder for him, but Obi doesn’t hesitate to shoot and scare her. there’s no way he would have missed in the competition with Kiki.
When Haruka hired Obi he knew what he was buying, but for team Zen Obi is selling himself as a highly skilled bodyguard, he doesn’t hide the fact that he’s strong and skilled but at the same time he wants to fit in with them without them wondering what he possibly did with such skills, knowing that people might pay high prices for someone like Obi to do the dirty job, so Obi doesn’t want to be put into the killer’s category.
Another reason for me to believe he lost on purpose is that this happens right after meeting Torou for the first time, after team Zen got a glance on his past, so he tries to fit in, showing that no way he is skilled enough to be a part of that world that they all fear.
But here’s the thing, Obi mainly wants to hide it from Shirayuki, he knows all of them are a bit familiar with that world and his act can only hold up so much against them, but he’s afraid Shirayuki would never accept him if she knew.
And since i’m still not over their reunion in chapter 88, i’m going to link this to obi’s behavior when Shirayuki ran to him.
here Obi barely gives the slightest information about him working in the underground, but he talks about the details of how he got the information like he was actually there. So after the long period of living peacefully in the castle, this part of Obi became more like a bad dream, like it never actually happened to him, but this reminded him of his sins and how he and Shirayuki stand on different ends of the moral scale.
Also, i believe Obi might still have professional connections with people from the underground.
That might turn back on him.
So whether Obi believed Shirayuki knew that he was in the underground or not, Obi almost lost all of the progress he had with Shirayuki and Ryuu and Team Zen.
To me here Obi’s face is saying “silly me” for thinking what he thought of Shirayuki hating him, but also that she actually still wants to be close to him. and that close up to Shirayuki’s face shows surprise and realization, she knows something happened. though he does sort of come clean when she gives him back the stone necklace, saying that he’s been through fights that could either take life or his opponent’s life.
but that’s for a different time.