That's often the case in real life too. For example, I only got into the job I'm in now by spectacularly failing the interview for a similar one, and subsequently working my ass off to get into a position that's ultimately better than the one I failed at. I've found it's normally the people who haven't experienced failure who end up plateauing earlier.
I mean he seems to know that he likes her by the last pages, but I'm guessing that it's not romantic love in his eyes yet because we are only 8 chapters in and god forbid a mangaka make a pair canon this early on.