I'm not looking for details to support my premise, I am analyzing the tweet. I don't know if it is a good way to show how cool you are or not, but I do know tha

I'm not looking for details to support my premise, I am analyzing the tweet. I don't know if it is a good way to show how cool you are or not, but I do know that it is more of a humble brag than merely self-disparagement. Really, you can just look at the tweet replies to see how his audience took it. If this tweet was really just self disparagement, you would expect the replies, if any, perhaps to be advice on how to hold a better conversation. Instead, you get people saying "I regret we don't hang out more", "Gosh, you make me smile", "This made me laugh, do the same to mine on various topics", and "I feel seen". He's playing to his audience by making himself look uncool to the general public. There's nothing wrong with this. It doesn't make him a bad person. But the fact that someone couldn't clearly recognize this kind of boggles my mind.