I'm not sure whether you mean gamble or handicap as they are two different beasts. For me, gambling is putting money on the counter and taking a position whereas handicapping is the art of matching statistics, situations, and human effort in an attempt to determine the team or individual mostly likely to win.
I love puzzles, so for me the handicapping aspect is infinitely more interesting and challenging. Once the bet is made and the game begins, it's out of my hands. Regarding betting, whether I lose a coffee bet or a large money bet, it hurts which is why I spend so much time handicapping sports I understand and avoid betting on sports I don't.