My mother sometime's picks up her friend's kid from preschool and it's then my job to play Mario Kart for a an hour or so until her mom arrives. Usually just the same two levels over and over. And I feel awful the whole time because she's trying really hard to race and gets up to 7th place or so and then drives off a cliff and falls back to 12th. And if I get anything less than 1st she gets upset that I'm trying to let her not feel bad. So here I am racing against a little girl, lapping her, and if I even slow down to lessen the distance between us she starts to cry.
Today, after an hour of that, I suggested we try Wii Sports Tennis. Much better. Do you know how easy it is to fake "Oh no! I swung just a second short!" It's a lot easier to make it a tie game or something more exciting for her. So lesson learned. From now on, only play games I can fake trying at.