We need to remember that he's not actually in a Romcom (in universe I mean, cause this story is a RomCom), he's just seeing a RomCom like situation...
Honestly, the heroine of this story (the losing heroine) is a big annoying, mainly because she has the easiest winning route and yet fails only because she can't take the steps.
She fails to notice that if she wins, she gets everything, but if she fails, nothing actually changes....