I don't seem to enjoy board or tabletop games much, or at least not all the time. I'm not sure why this is. Part of it might be that I kind of suck at them, and losing all the time has a way of draining the fun out of games. For me, the process of playing has to be fun, regardless of whether I win or lose, and I don't see that many games with fun-to-play mechanics. The fun is meant to come from winning, but that can only happen for one person, usually. If your board game is only fun when you're winning, then, for a four-player game, that means your audience is 75% not having fun.
Now, for some people, trailing behind has this kind of invigorating effect. Their response to losing is "Must Try Harder, Must Play Better", and that push - the pressure to do better somehow - is a thrilling kind of fun for them. For me ... I don't know. Maybe I'm over-competitive in my own way, but losing at a board game and knowing that I'm losing is pretty disheartening. It doesn't spur me on to greatness, it puts me down in my place. "Look, you're losing! See how much you suck? This is how much you suck." It might be and expression of depression, too. Even knowing that depression lies, though, is not enough to pull me out of the losing-and-sucking funk.
So what do I do? We only have about 4 games that even work with two players, which is how we find ourselves most of the time, and most of those fall into the "win or no fun" camp. Many of the games we play also seem to derive their fun from composing and enacting a complex and cunning strategy for winning, and I guess I'm not quite there yet, either. I need more games that are just fun to play, win or lose, or at least games that could be won or lost right up to the very end, and it's anyone's guess who the winner might be until then.
Mokalus of Borg
PS - I also don't seem to play many video games.
PPS - That's probably more because I have so little time at home on the computer.