I was playing Which Way USA with my daughter this weekend and found it to be fascinating. In this game you move around the board picking up your tokens and the first one to get back to their "home" and answer the question there wins. In order to pick up a token you have to answer questions about the various states.
As we were moving around the board I was having a good time. I answered some questions right and got some wrong. But I had fun and learned some interesting things about the country. I won the first game by a couple rolls and my daughter was not pleased.
She asked to play a second game so we did. During the second game my luck wasn't quite as good, I got more questions wrong and we were running neck-and-neck pretty much throughout.
Although our game pieces were running neck-and-neck, I discovered that I was actually way ahead. I learned some more facts, remembered some answers from the first game and generally had a good time. My daughter, on the other hand, did not have a good time. She was frustrated about losing the first game and her frustration kept her from remembering facts she had learned in previous games. Her frustration ruined the game for her.
In the end she got "home" first and answered the quesion. And while most people would say that she won I really don't think so. I think that I came out ahead. I would rather come in second (or third or fourth...) having a good time and learning something than to come in first without any enjoyment or increased knowledge.