I think the problem with this is how hard it is to sell someone being funny. Like apparently this girl is his idol someone so unbelievably funny that some people think she was an up and coming comedian but like...
Lets be real, shes not any funnier than the average user you chat with on the internet. Its easier to seel immensely smart and physically gifted than something as subjective as this. And maybe its the translation runing it but i doubt this could be that much funnier in the original text.
Aside from that, the interactions themself are entertaining and believable enough and the story flows well.
The bit in the diner where she goes "this is where hard working dedicated types vompete with prodihies" is kinda weird and its hard to get a read on the fmc in general but im willing to give this a cpuple more chapters