On page 15 I had flashbacks of the infamous "I don't understand" childhood friend rant from Inou-Battle wa Nichijou-kei no Naka de, except here the genders are swapped between the childhood friends and he held back from going into a 3-minute rant to ask her to just outright tell him what she wants.
The conflict in this oneshot is, it's getting harder and harder for him to guess what she wants, which culminated into page 15 with him about to beg her to just say it. But instead of resolving the problem where she finally properly tells him what she wants, she just cries and then he caves, returning to the status quo.
Would've been awesome if she realized she was giving him a hard time all along, until he swerved into "I just don't want you doing this to other people" and then he went back to enabling her little guessing games. Well, you do you. I guess he didn't want his problem solved. Not much really changed except for her confirming he has feelings for her. I wanted to like this, the art is fairly cute, but... it's more annoying than satisfying to me.
Also I wouldn't call him dense when it's her who's clearly and consistently failing to communicate properly like a human being...