Jasmin Nena Garcia answered Venessa's question 6/6/2012 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? Tell him how you feel, that you don't want to be with him, but if you say that he will break your stuff, when he goes to work move everything out that's your's and after just tell him and give him the apt key! Hope it works out for you.