My Ex girlfriend is trying to sue me for a unpaid dental bill that she paid for in December of 2010. The issue is that her and I had made an agreement that if she help me paid my dental bill then I will put her on my health insurance. Well in July we had broken up and she took herself off my health insurance, which was her idea. The thing is that we were on good terms and she complain that she needed money for a trip back to her home country to see her sister get married so I agree to help pay some of the bill because I felt bad for her. Our relationship got worst and now we restraining orders against each other now she want to sue me for the whole amount. So do she have a chance of winning the suit she has proof that I will help her pay but I have proof she was on my health insurance and $250 dollars a month was being taken out of check to have her on my insurance. What should I do should I counter sue or should I see what the judge got to say.

...should I counter sue or should I see what the judge got to say.

What would you counter-sue for?

If I understand what you are saying, she paid your bill in return for your putting her on your insurance. You did that, and thus fully performed your side of the agreement.

See what the judge thinks.