The thing that made Living Game great was that it wasn't really about will they or won't they get together. They were pretty much officially together from like, book 4, and he figured out she liked him by like, book 2. It was about them being able to make their relationship work, despite their age differences, and problems with money, careers, friends, etc.
I think one of the simplest scenes in living game kinda sums the whole show up. When she's trying to get the money for college, and so he tries to give up smoking just to help save that eeextra little amount. And it makes him miserable and grouchy, but he keeps doing it anyway.