How to deal with an insecure guy friend?

Anonymous
After knowing him for awhile I’ve picked up on how insecure my guy friend is. First he assumed that I was already taken and made a little snobby comment about a guy that’s my lockscreen who was from a music band.

Next, I gave him a compliment about his hair (He wore braids) and then the next week I saw him he took his braids out and kept it in an afro ever since. Then, he would wear a new mask and whenever somebody said something about it (good or bad) he would go back to wearing the standard surgical mask. I once complimented his red mask before and of course he stopped wearing it the next day.

Should I try to encourage him to be more confident or stop being friends with him? His other buddies even make fun of him for liking me and he’s been keeping his distance from me too when they’re around.

And he says he doesn’t care about certain stuff, but why would he say that if he cares about other people’s opinions on what he wear and who he likes, etc? If he wants to date me I can’t be with a man who’s very insecure and miserable. He’s sweet and I know that everyone is insecure about something but it gets annoying with him.
How to deal with an insecure guy friend?
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