How to help 4/5 YO through relationship with his friend

[Ahbegyuhpardun]

My son has a friend in school. I'm good friends with his mum too and they have younger siblings the same age.
When they were first friends it was quite physical and my son came worse off during some spats/playfighting.
He's now saying he's always wrong, and is quite sensitive if you correct him on something. It then always goes back to... He's always wrong, his friend is always right and he knows nothing.
Now I don't know how to approach this. I want him to be resilient to knock backs, and also there's the fact that he isn't always wrong!
His friend is very bright and can be harsh (like most kids) when they're disagreeing. One example is they were colouring together... My LO has never really been into it, so was giving it a go but not staying in the lines etc. And his friend turns to him and says... You're not colouring, you're scribbling.
Technically he was right! But I think the constant put downs are getting to my LO.
His friend is always the leader in the playground, and my LO is the wingman.
But when you try and broach the subject of him trying to find new friends he is adamant that he has to be friends with this boy.
They're also sat on the same table because they're in the same skill set (groups of about 5). So he spends quite a bit of time with him.

How do you go about instilling some confidence in them? And getting them to realise being wrong about something isn't the end of the world? Oh and also maybe trying to avoid people who make you feel bad about yourself. I've encouraged him to stick up for himself and started him in judo to help build confidence and also use up that energy so he's not so obsessed with playfighting (which has definitely settled down now). But it's now at the stage he just screams and goes in a huge strop every time his friend upsets him. So he's not even sticking up for himself he just comes a cross as bratty. Although originally he was internalising and I could see him just shrinking into himself and going quiet. I don't want to say the wrong thing, or make too big a deal of the small stuff either.

As you can tell I'm quite wordy and into feelings, but he's like his dad and doesn't respond to that. So I'm not sure how to help him through it.

I think it’s a really common dynamic and that you’re doing the right things to help your son.

I guess you could help him to develop confidence by asking for his view on things regularly and help him develop leadership skills himself. A bit of relaxed role play can also be helpful.

My DS had a friend like this at 4. I worried like you. 3 school moves later (both separately) they are best buddies at 12 and still like chalk and cheese. Friend is still centre of everything, bright, high achieving and ‘out there’. DS quietly gets on with his own interests, loves the confidence and different experiences that being around this friend gives him, and appreciates the peace when he’s gone home!
It’s the sweetest friendship and I’m so glad I enabled it through the school moves.

Following as I have a similar problem although they go to different schools luckily. Similar age to yours although my friend’s child is a year old than mine.

i avoid play dates now as it always ends up with an issue and my child coming away feeling bad about themselves. My friend’s child says stuff like “my picture is better than yours isn’t it?”, screaming “you lose” in my kid’s face, constantly changing the rules so he always wins etc We have lovely play dates with other friends so I’ve decided it’s easier for us to not see them.

I used to explain to my child that what her friend had said wasn’t very kind and model what kind things we could say but it’s really hard to know what else to do.

Regarding play dates when they were little, I both other mum and I did supervise quite a lot to support them. So we’d play board games altogether or sit at the table doing crafts or whatever. Then we could both be modelling and supporting. We were both conscious of the dynamic - although it’s hard to intervene with someone else’s children, we trusted each other to do this.