How to coach son into behaving around new people/friends

[MissRachelismycoparent]

My son is 8 and is a lovely, affectionate and kind child. I always see the best of him when he's 1 on 1 or in his familiar family environment. He's always struggled around new people and making friends, almost like he doesn't know how to behave around new children and adults. I've noticed recently this has turned into him boasting/showing off. It really makes me cringe when he does it. I think he's doing it as he's trying to be 'cool', seek attention or gain a friend. For example yesterday at the park someone asked about our holiday and he kept butting in saying 'it was 5 star, it had 7 pools' etc and I just felt so embarrassed. He said he did it to get them to like him.

How do I speak to him about how it's not good to show off in a kind way and also prompt him into how to make friends?

Was it 5 star with 7 pools? All kids get excited and show off about things.

My friends have a just turned 8yo and I notice it with him and his friends when they meet up in the park - most of them seem to do it, their conversations involve a lot of talking about themselves, their interests, and what in an adult would be considered boasting. "I went to [fun cool place] yesterday, I'm going to [fun cool place] tomorrow, I got a new water gun, I can do what you just did but jump twice as high, etc". You can encourage them to be polite and ask questions and have a more "adult" conversation, but it's called adult conversation for a reason! I think the social niceties don't really kick in till they're a bit older.