I think the thing about social skills is that a lot of it is about unlearning, rather than learning. Let's say you're chatting with someone you don't know, one

I think the thing about social skills is that a lot of it is about unlearning, rather than learning. Let's say you're chatting with someone you don't know, one to one. You feel like you don't know what to say, so you try and think of something and move the conversation in a new direction; maybe you read a little bit online about social interactions and try to use that in your conversation, but it feels like it falls flat. My experience is that this is because each social interaction you're having is a call for you to become more aware of yourself. At the point when you felt like you didn't know what to say, maybe you were filled with anxiety or shame, maybe you felt humiliated that everyone else seems to know these rules for social interactions that you don't. Maybe you felt uncomfortable about the other person's body language. So, rather than trying to learn basic social skills, you need to learn more self awareness, which will eventually lead to unlearning the anxiety or shame or whatever else came up during the interaction. This will give more space for you to be present with the other person, and you can look for a sort of flow to the conversation. Next time maybe you just leave space for a couple of seconds and they continue the conversation, or something fun pops it your head spontaneously. It's not about trying to find the rules that exist that everyone else knows, it's about trying to find the you that exists underneath your anxieties and pain and other difficult feelings that you haven't yet delved into or fully experienced. I think generally being blocked up in social interactions is due to unresolved experiences earlier in your life, and I found that psychotherapy helped me a lot with this, and also meditation and yoga. Also, some social interactions are a lot more complex than others, for example more people may mean more complex (although some people may find group situations easier).