@FireCamp I think he was the childhood friend of F-cup and he always liked her. So, he'd like it if Naoto and F-cup-chan broke up. He's the kind of character who is in the background, offering support to a friend. While patiently waiting for him to fail, so he can swoop in get what he truly wanted.
I think he and Satsuki at one time "teamed up" for a short period, so they could both get the person they liked.
It's quite possible he'll try to get her back, or he could be pulling his hair out wondering what went wrong. Now, will F-cup-chan pretend nothing happened, or go with the whole "break up"...