It's really silly that he thinks he can only confess after winning with no handicap. It's even a little condecending. She's been playing a long time and she's really good. He's only just started but decides he can't confess unless he's as good or better than her? He's seriously belittling something she loves so much. I know him wanting to be superior before he confesses isn't the actual message the author is trying to send but it really comes across like that sometimes. It's really just a plot device to stretch it out longer and show his determination. It's just hard not to see the other side sometimes. If I was her I'd be kind of annoyed, all that lost time just because of his pride.
Otherwise I do love this series. It's great to see the girl being the one pressured for once. You don't often see it, it's normally the guy losing his spagetti all over the place while the girl just goes "huh, okay" then is immediately okay with their love. I always love those moments when they realise it though.