destiny Cheesman answered Venessa's question 6/25/2012 Trying to break up with my boyfriend who I am living with. I tried to break it off once but didn't work, I'm too nice. Most the things in our house are mine and he would go crazy and break my stuff. How should I go about breaking up with him? I honestly think you should just sit down and talk to him. Explain why you need to leave. And let him know that you don't want to be with him anymore. When he tries to break your stuff make him stop.