I see some people here feeling disgusted by the MC and their antics. This is totally justified, as the pretext is well hidden and isn't very explored in the anime. If you read the author notes, you'll see that the MC is actually under a curse: He MUST ask to see the panties of every woman he meets and interacts on an emotional level. That explains why he goes out of his way to ask this even to girls that clearly show interest in him. He can't go further. He has to ask them or they will be under danger. That is the curse bestowed uponhim.
You may have noticed that the anime is filmed from the MC POV. Other "questionable" animes draw the MC with hair occluding their eyes. Then why? Is it to gain immersion? Well, this is again to hide the emotions the MC shows. For example, at the beginning of episode 5 the girl says the MC is not paying attention. He has a distant look, because he is thinking about what's going to happen now. It's out of his control. He has to ask her, and he will probably lose his relationship with her over this. His dearest childhood friend. But he has already made up his mind. He has to protect her. And so he does the deed.
This anime is very sad when you realize the hidden reasons behind the MC actions. It makes me feel sorry for him. At the last chapter he almost got his redemption, but it was futile in the end.