Honestly, something is off with his face. It looks like he has had cheek implants as they are very round, full, feminine, and not at all masculine. They dominate his entire midface.
I agree with him getting surgery though as indeed his smile does look quite bad, and if he's willing to do it then why not.
I noticed also the extractions lol, I wonder what effect that'll have on his aesthetics long term.
All in all I think his biggest issue is cheekbones too feminine. Makes him look like a freak.