Don't really know how this has come about or how to explain.
I feel like ds of going to push friends/ potential friends away. He's trying to be nice or funny (or thinks he is) but sometimes every comment that he makes is negative or a put down as a joke.
He's not meaning to put people down, but he does. Sometimes I know it's insecurity - teenage years are difficult. For example, to make conversation he might think about something embarrassing that happened to someone and retell it as an anecdote. This means the person is embarrassed, but has to laugh politely.
If confronted, he acts superior and argues back, no matter the company. It's like he's lost all awareness of how he's coming across.
I've tried telling him that it's never good to make people feel embarrassed - or to have to laugh politely, but he just doesn't see it. He thinks they're laughing with him. He doesn't see that they're just being polite, but feeling awkward
Other times, it's 'smart comments'. Not meant badly, but just not nice.
I feel it's got worse over the past 6 months or so and I don't know what to do.
His intention isn't bad, but it all always comes out wrong. He never used to be like this.