When playing games with little kids, I let them win most of the time. Not all of the time, because they do need practice at being a good sport. I remember the first time I played Chutes and Ladders with one of my boys, when he was about three. I let him win a couple of games, and then I won. He got soooooo mad! He threw his game piece across the room, shouted, “I hate this game and I’m never playing again!” Then he stomped off to his room. Once I stopped laughing, I made him come back and help me clean up the game. I said, “Everyone loses sometimes. If you’re nice about it, people will still want to play with you and you can have another chance at winning.” I think he had to lose a couple more times before he could handle it without a fit.
Losing all of the time is not fun, and let’s face it: Most little kids are going to always lose when playing against an adult. My husband and I both let the kids win just so they continue to have fun and learn to improve. When they do lose, we explain to them how they could have won, and give them tips on doing better the next time. Our daughter is ten, and we don’t let her win anymore. Most games she has a very fair chance of winning on her own.