[More than winning and losing, what gets him is that she's as good as she is to start with. Pretty much since he's never known anyone who could keep up with him.]
I guess we'll have to up the ante.
[A bit wry.
However he then pauses, frowning slightly.]
You have a point. I suppose they really can.
[He really hadn't been thinking about it like that. Those twenty years are all on her side (leaving him to feel a pang of guilt).]