The little guy is super fun to play checkers with. He's likes it a lot and is real strategic about it, certainly better than any 5yo ive seen.

I end up beating him most of the time but he's actually taken me a handful of times and it was astonishing. He's a capable player for his age. He's going to beat the pants off me more often than not in the near future if he sticks with it.

For most other things I dont give complete effort to just crush him but I also dont just let him win easily. We definitely don't gloat about winning.

If he loses with a bad attitude I make sure he understands that "nobody wins every time. Everybody loses and thats ok, we aren't going to have a bad attitude about it. We keep trying".