At this point you have to be pretty stupid to not think she has feelings for you.
Even for someone with super low esteem, the fact you can even bring yourself to talk to a girl, and one who wholeheartedly wants to spend time with you, should be a huge red flag that you should give it a shot. But fine, maybe he's super shy to even ask, but even so, the fact that he's brushing it aside for this long makes me wonder how much longer the author can milk this.