I read the book and didn't like that either, the entire plot felt like wish fulfillment for the author. "What if there was a world where my vast knowledge of 80s trivia would make me rich and get me the girl!"
I know I'm going to get burned for this, but I actually liked the film better. The "omg I'm a pop culture genius" vibe of the book was much less present, and the same goes for the "win the game, get the girl" element. Still not great, but better than I expected.