AIBU to have corrected my 5yo on this?

My DP genuinely loves playing with our friends’ children (we don’t have our own) and he’s not ‘odd’ (or if he is then fine, it’s a kind of odd that he’d be happy with). They adore him back.

Anyway, OP, you did fine and some people are being harsh. You made clear what you meant and emotionally supported your DS. It does sound like he needs ongoing support with resilience, but, as you say, you’re working on it, so I’m sure it’ll come in time.

He didn't say anything bad about her at all. He wasn't unkind. He voiced an opinion.

If she was bossy, it's not exactly surprising that he won't miss her. She should have been told not to be bossy with your children in their home.

I wouldn’t overthink or replay this with him. He’s not going to suddenly stop going to you as his “safe person” and it was reasonable to remind him not to say potentially hurtful things in front of the subject. It won’t do him any harm to have been a little bit upset and ultimately you’ll be doing him a favour by gently helping him build more resilience to this sort of thing. He sounds like a really lovely empathetic wee boy but he won’t go through life without ever doing wrong/being upset etc As long as he knows it was no big deal and that he can always talk to you, and you’ll always think the world of him - he’ll be okay!

If he didn’t like her why did he play with her all weekend? Apart from maybe a few odd people, most adults do not genuinely love playing with children, especially ones that aren’t theirs and most play is instigated by the kids. I love my stepkids and nieces and nephews and play with them lots but if I could genuinely choose, I’d sit on the sofa and drink my tea while they amuse themselves rather than climbing on me and asking me for piggy backs 😂. I’d never say that though. What I would find irritating would be if a child who sought me out to play with then moaned and said they didn’t like me. Fine, cool, you don’t have to like me but leave me to chat with the adults then and ignore me. I feel bad for this poor woman who has made a big effort and then some kid make a rude comment. I’d have told him what you did too and I’d have said if you don’t want to play with her, you don’t have to but if you choose to, then don’t say unkind stuff about her afterwards.

YABU

You want your child to be able to tell you what he is feeling.

He won’t do that if he feels you will shame him for his feelings.

There was nothing wrong with what he did. In fact he did it the right way. He waited till the person was gone and then shared his feelings with you, his trusted person. In anything, you should have praised him for his consideration in not saying this to or in front of the person in question.

The adult is at fault not the child

I'm iffy about you telling a 5 year old not to voice negative opinions about an adult. He waited until she had left and said it to you, his mum. He should be able to voice his feelings to you.
Seeing as though he is very sensitive I do think you need to revisit this with him. He needs to absolutely know that he can come to you about anything.

I wouldn't have bothered having that conversation in this context. Clearly he had been feeling that way for a while but managed to wait until she was no longer there to tell you. In my opinion that was quite perceptive for a young child and he's already been mindful of her feelings (even if it was inadvertently). He told you as you are his mum and that is to be encouraged.

My eldest child is very much like this and I find I have to stop, think and frame my words in such a way that she knows I'm trying to teach her something rather than tell her off iyswim.

I don't think he deserved any criticism at all. I'd have told the relative to stop being overbearing with them at the time. He will keep stuff to himself if his mum doesn't have his back on these things. I'd just have agreed with him. You are expecting him to have more maturity than most adults at 5.

This ^^

I think it is very important that you talk to him about it, starting with an apology for saying he shouldn't have told you that, when it was absolutely the right thing to do, and that you are very proud and pleased that he told you, and that he waited until the annoying lady couldn't hear him. Then you can tell him that you agree that she got a bit bossy didn't she, and then if possible offer him a little treat for Mummy getting it wrong at first. I do think that you do have to "big up" his good and sensible reactions.

I'd have asked why , too.

This.

Your dc should always be able to tell you when someone makes them feel uncomfortable. If he’d said it in front of her I’d have had the conversation about hurting people’s feelings but he didn’t, he said it to you privately. He needs to know that he didn’t do anything wrong. He doesn’t have to like everyone.

I think it was fair enough he expressed his opinion, and knew not to do it in front of her. He's only 5 but that's quite mature.

I agree.

We had the concept of "inside thoughts". Things that were absolutely fine to think, but would be hurtful if said out loud.

Exactly. It won’t encourage him to speak up if, God forbid, he is treated badly or worse by someone in the future.

I didn’t really mean make fun, rather just a little chuckle 🤭… although I realise this needs to be done sensitively!!

No wonder children cannot think for themselves, if parents are policing/mediating their thoughts.

He was perfectly right and very polite.

I would have said "I know, right", and then explained why, even though the woman was difficult to deal with, she possesses x, y, z qualities that make her a better friend than someone who says the right things and calls me "hun/lovely"

He did absolutely nothing wrong. As PPs have said, the best response should have been to ask why he felt that way, and then to talk through that.

I think it’s hard in the moment. But he was expressing his feelings about her to you. If someone was bossy with me I would probably be pleased they were going home! I would chat further about why he felt that way. Plus she did t hear him say it. So it’s ok to express it.

His comment deserved a good laugh and an exploration about what he won't miss about her. He's clearly a bright kid as he DID remember not to say it to her face and said it when she was gone. At this point be honest with him, tell him that you were a bit shocked by his funny comment and got a bit bossy yourself but you would be interested to hear what he found hard-work about this friend. Reopen the communication otherwise he's at risk of not opening up again in the future.

Always be curious about your children first before worrying about imposing learning.

I would have laughed my head off, agreed with him and then said make sure you don't repeat that in front of anyone else. Your response sounds incredibly serious. It must have made you at least crack a smile?!

I would have acknowledged the thought, explored it and then praised him waiting until she was gone but reinforced that he can always ask to talk to me privately if he is scared. As an example...

"Oh really? Why's that? Yes I can see how that came across. Let's be glad it's just us again. It was very thoughtful of you to wait until X had gone so her feelings weren't hurt but if you are ever worried or sad you can always tell me. If it might hurt someone's feelings or you're scared you can ask me to come to your room and we can talk in there. Right, time for [lunch/shopping/other activity]"

I don’t think this should be seen as a telling off, it wasn’t. You gave your son valuable information that will help him. Not all of these types of conversations will end well, but as long as you do it how you did (balanced, kind, etc) he will benefit.
I have two extremely sensitive SS’s (13 and 15) who have been given very little corrective feedback throughout their lives (for want of a better expression) as they would cry, withdraw, etc; they have little to no resilience and struggle to cope in so many situations (asked to tidy, apologise if they’ve upset someone, school, etc).

Developing Emotional intelligence and being able to discuss positive and negative actions, thoughts, emotions will help your son hugely. There are so many ways you can help his confidence and feelings of self worth, but avoiding these conversations will not ultimately help him. Difficult conversations are an essential part of life and can help healthy development if done correctly - which it sounds like you are!

Don’t beat yourself up, you and your son sound lovely!

He’s very aware of hurting her feelings to have said it away from earshot.

I don’t think anyone at all in this story has done wrong.