What do I do if my closest friend stresses me out with his insecurities?

Anonymous

They don't admit to their insecurities, and they ask me to be honest which I do, and always do to relieve any misunderstandings. But I sometimes feel like I am always doing something to trigger their insecurities. I mean they haven't admitted to it, but I sense it with how they behave. For instance, they recently got into texting me daily which I was flattered with, they rarely like to reach out and start conversations with anyone, so I was happy they were making some progress. However, when our conversation died out, they just said "ok have a good rest" even though I was not sleeping, and I gave a short reply to them in our group chat afterwards. I did tell them in our DM I was not sleeping for another 30 minutes but I let them go. Then they called me "evil", which I was assuming they thought I did not want to continue the conversation. I didn't continue the conversation either because I was going to sleep anyway.

That is just one example, but I feel like they need a lot of reassurance and me recorrecting their assumptions. We both agreed texting we misinterpret things, so I suggest calling but they get awkward with just random calls and chatting? I don't know what to do, because they are a really good person deep down inside, but their behaviour and them thinking I am mad at them or I don't like them, makes me tired. I don't text them everyday anymore because I get too drained and need my own personal time

What do I do if my closest friend stresses me out with his insecurities?
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