Going easy--but not too easy--keeps his interest. You don't want him to have too easy a time, but you don't want him to keep losing.
Is it ok that I let my five year old son beat me at chess

Teach him how to mate with KQ v K or KRv K. That way he can legit beat you and learn an important skill in the process.
I normally think it's demotivating to let kids win (because they'll know you're doing it)... but 5 is pretty young so now I'm uncertain heh.
I like SilentKnight's idea of letting him win... from a won position. Starting out with tactical type positions and let him find the best capture I think would be more useful than starting from the opening position. Or mazes where you e.g. move a knight to capture all the pawns trying for the shortest route.
But at that age I guess just playing is above average work on chess already.

Five years old - of course you're overwhelming to him and he knows that you're the much better player. So yes - do let him win often to keep his interest - and sometimes take his piece and checkmate him when he goes wrong.
Keep it a game - but make it so that it's a game for him - that he can win if he plays well (relative to what he knows), and can lose if he fouls up.
Five year olds are very much into games.
Losing all the time is not a game and will not help him - he will turn to other games...
Capablanca started playing chess at age eight. His physician warned his parents that he should not play before that age (after some unbelievable successes at ages four and five).
So yes - easy is the way to go.
Carlsen showed casual interest in the game as a little kid - and at age eight, too, he started to devour books and quickly improve.

It's up to you, but maybe you should beat him while you can, because if he practices, soon he'll be better than you. Should take only a couple years, provided he gets into it. Kids improve quickly. See if he enjoys it!

I would say more like beat him every third or fourth game and mostly let him win...
After he builds up a habit of playing chess and feeling like a strong player - you can then tell him (maybe several months later) - now that you can play well, I will be harder on you. Then you can start beating him half of the games, and he'll mature as a player and as a person.

It's interesting to see both ends of the spectrum in play here. My father never let me win, not once in my life, until I finally just starting beating him, and then I have never let him win since either ;).
I beat all the older kids at my playground clubhouse, that's where I got my "feel good" moments, but I always respected my father for not catering to me in this regard. When I beat him, I knew I had truly beaten him.
This is how I handle things with the 5 year old I am sometimes teaching: I play one "normal" game, then for the next game I take all the pieces off the board and only play with king and pawns and see she if she can mate me. When she can do that consistently, I will add the 2 knights back in, etc. By alternating games she should not feel like I am crushing her constantly, etc. But I never play purposefully bad or mediocre moves in games with her.

<Btickler> your approach with the 5 year old is great. You found an original way to make a game of it - when the result isn't known beforehand - but without compromising your own play.
You force her to plan and to have a certain idea of what she's doing, then gradually step up difficulty. I like this approach.

<Btickler> your approach with the 5 year old is great. You found an original way to make a game of it - when the result isn't known beforehand - but without compromising your own play.
You force her to plan and to have a certain idea of what she's doing, then gradually step up difficulty. I like this approach.
Thanks, now if I could just get her to play Chess as often as she watches Pokemon ;)...
The funny thing is, playing with just king and pawns vs. a full set has actually taught me a nuance or two of what you can do with pawns in a pinch ;)...

Oh - so it's your daughter :-)
Mine likes the game - we spend some time over chess now and then, one of her many interests. She's close to 12.

i used to teach judo, with kids I had a method that was very effective.
If they are doing evrything correctly, as they were taught, I will always let them succeed. I'm a big guy and if a tiny little kid steps towards me with their feet in the right place, they turn their hip correctly and apply pressure in the right direction, I will leap over them and CRASH into the ground with as much noise as possible. It's a moment that makes a strong impression.
If the kid is trying hard, but not getting it right, I hold the line, we discuss it as we go, "what's going wrong? why?" let them work to figure it out.
If the kids not trying, or not payong attention, I just push them over (gently) to show them just how weak on their feet they are.
So my advice is to reward good work. If the kid is displaying learning allow them to succeed. Just make sure the lessons keep advancing, and the student will keep advancing, no matter how much you let them win.
When playing from the starting position I set an objective like castling or finishing development. Then if they do it, I praise them with something like "that game was a lot harder for me because you finished development in the opening, good game." But if they ignored my advice I don't say anything.
Just because you win, doesn't mean you can't be respectful and encouraging. I guess that would be my main point when you're not a paid coach and you mostly want to keep their interest.

The first time I "beat" my father at chess, I got mad at him, and told him that I knew he let me beat him. It may have taken another 20 or 30 games, but next time I beat him, it wasn't because he let me win.
The first time I "beat" my father at chess, I got mad at him, and told him that I knew he let me beat him. It may have taken another 20 or 30 games, but next time I beat him, it wasn't because he let me win.
Yeah, probably depends on the kid. My dad never let me win and because of that it was fun for me to try.
I know he's only 5 so I don't expect him to be a tactical player or anything yet. Just wondered what the best approach is.
Thanks