Do not live with boyfriend and rely on family assistance with school/car 2. You live with your boyfriend, and she pays for your education and automobile expenses. This, in my opinion, is fair, and the decision is entirely hers. Even though my kid is just six, we are all about framing things as choices and consequences. That lifts the burden of "I'm the terrible person" off my spouse and me. We're just trying to help our children learn from their mistakes. 3. Stay up to date on school requirements and be sure you are aware of what living with someone means before you agree. If it turns out that school policies change or that she doesn't qualify as a roommate after all, you have been informed of this ahead of time. 4. Talk to your child about their decisions early and often. Let them know that you love them and support their efforts to find a place they can call home, but also let them know you want them to feel comfortable enough with their choices to seek guidance if needed. 5. Find a good counselor you can talk to together. Someone who will understand both your views and your child's so there isn't any bias. They should be able to help guide you through any difficult issues that may arise during the process.