Maybe because he knows she doesn't see him as a man, let alone have any romantic interest in him. Maybe he knows that she would probably think he was just trying to make her feel better after being dumped by one of her numerous boyfriends. Maybe he knows she would just laugh histerically. Maybe he knows, but doesn't want to admit, that she isn't worth his time or love.
Woah that escalated too quickly..
Well damn
He did try confessing to her a few times, but like any other typical shoujo manga the timing was seriously off. Luck wasn't on his side
╮(￣▽￣)╭
Why doesn't he just confess....?