By male oriented romcom standards, Nozomu IS a natural when it comes to complimenting girls. I'd say there are a lot more protags who can't do what he did than there are who can. But then, he really only managed it because he doesn't see Shiori as a love interest.
Personally not a fan of undercuts, but hey I'm not Nozomu. If he finds that pretty, more power to him. Glasses girls, though...