I have tried to get a guy I know to understand that I am not interested in him, but he just assumes I am playing ‘hard to get’ which is frustrating. He isn’t troubling me, nor do I feel threatened, but it feels as if I am unable to make myself clear to him. I don’t know if I am giving him mixed signals by continuing to chat with him, because we have been friends for a few years, but to end all contact seems a bit harsh and unnecessary. This has been going on for four months, and he tells me to take all the time I need. It only makes our meetings more awkward, but he doesn’t see that from my perspective. How do I get him to accept that my decision isn’t going to change no matter how long he waits?
This has nothing to do with your ability or inability to send him a message, and everything to do with his refusal to accept your decision. It is disrespectful and uncalled for, and you shouldn’t have to blame yourself for his behaviour. Yes, losing a friend for something like this is sad, but it isn’t your doing. Tell him that you are considering ending this friendship because of what he is saying, give him a chance to accept your decision like a mature adult and, if the awkwardness continues, write this off as one of those unfortunate circumstances where you were friends with an immature child. 

My boyfriend recently asked me a question about justice that upset me, and I overreacted. He was just being hypothetical, but it angered me. Since that conversation, he has been wary of saying what’s on his mind and I am upset because I think I damaged our ability to communicate freely. I know I shouldn’t have overreacted, but I was caught up in the heat of the moment. How do I fix this?
Communication takes work, but time should smoothen over these rough edges. Give him some space.