“I almost feel like it’s because I’m afraid of judgement, but I feel like that just doesn’t make sense. It’s irrational for me to fear the judgement of people who love me.”

– On a very deep level it makes no sense whatsoever, because their judgements about you are totally irrelevant to who you are. If they think you’re great that doesn’t make you inherently great and if they think you’re stupid that doesn’t make you inherently stupid. But on a more superficial it makes a lot of sense because you have something to lose with these people, i.e. a close friendship. When you speak to a stranger you have nothing to lose and everything (potentially) to gain. When you are speaking to a close friend you might lose their friendship. They might start disliking you.

The way out of this is to stop caring whether or not they like you and to prefer to have the friendship rather than feel you need to have it. This is a shift in perspective and your ‘way of being’ in life. Easier said than done of course but it gives you an idea of what to work on.

Once you come to realize that you can be happy with or without these close friendships, then you will know you have nothing to lose. How comfortable are you being alone? Can you be alone for long periods without believing lonely thinking? If not work on this – start spending more time alone, maybe in nature, maybe going to concerts etc. Why? Because when you are 100% comfortable being alone, you won’t ‘need’ close friendships any more, you will simply desire them. So you will be able to handle the thought of losing your friendship. In addition when you realize that it doesn’t matter what anybody thinks of you, because their thoughts don’t define who you are, then you will stop fearing them disliking you and so this neurosis will also dissipate.

Here’s a quote from Keith Johnstone’s book “Impro”: “The brain constructs the universe for us, so how is it possible to be ‘stuck’ for an idea? The student hesitates not because he doesn’t have an idea, but to conceal the inappropriate ones that come uninvited.” In other words you are probably rejecting possible conversation ideas and saying “No that’s too boring” or “No they might think this of me if I say that” and that means you have no ideas at all. Just say whatever pops into your head. It doesn’t have to be interesting. Why would you need people to find you interesting? Have you signed a contract saying you will definitely be interesting all the time? Do you think this would even be ‘preferable’? What about things you find ‘boring’, the other person finding ‘interesting’, and vice versa? If it’s so subjective why are you worried about finding the “right” idea for a conversation? Have you also considered that boring conversations can turn into interesting ones, the idea that you start off with small talk and then turn it into something deeper? A lot of conversations begin with “How are you” but quickly become more than that. Would they become more than that without the opening “How are you”? But is the “How are you” inherently interesting on its own?

Even better, next time you have no idea, say nothing and be 100% ok with it. Sit there entirely comfortable with your not saying anything. I notice you take 100% responsibility for the conversation, why? A conversation happens between two or more people, so why are you trying to be the one who makes it interesting? Why shouldn’t the other person have this role? It would be a bit weird of you to assume that the other person must ALWAYS be the interesting one, so why are you burdening yourself with this unrealistic expectation?

Be comfortable with silence. Sometimes sitting with another person and saying nothing can be deeper than anything else. Your presence alone is powerful, you don’t need to fill up every dull second with another bit of speech. The people who are really comfortable in their own skin can have much silence.

If you want better conversation ideas, become very interested in what the other person is saying. Ask them questions about what they’ve said. One of the most powerful questions is “What kind of X?”. So if they say, “I’ve got a new dog!” you say, “What kind of dog?” They say, it’s a spaniel. “What kind of spaniel?” They might tell you its colour and size and age. You can use the “What kind of X?” question a lot. As long as it isn’t the only thing you say then it sounds normal and is great for eliciting more information. Become GENUINELY curious with what the other person is saying and time will fly. People love talking about their own lives. Once you get them started and keep asking questions they will never stop!

All best. Good luck. You have loads of perspective and ability to be introspective about your experiences so change will be very possible for you indeed. But maybe the real power comes in knowing you don’t have to change anything, just become more comfortable with what happens.