I lent money to a friend in a series of installments. I did not request loan documents as his ship was aways coming in the next day. Over the course of the last 18 months, I have two loan documents. The first was produced by him which acknowledged the initial loan amounts about 16 months ago. I did not sign it as I was unhappy with some of the terminology. But I lent more money after that document was presented and we agreed that the loan amounts were indeed loans, not gifts. I produced a new loan document and he did sign it after deleting a number of key protective clauses. I have not signed it because I am enraged that he is offering no security whereas he did offer security for the first proffered document. He also changed the due dates, etc. Additionally, he made at least two wills and I'm sure he has had neither witnessed, putting me as a beneficiary for the amounts owed. I have copies of these. I have countless emails from him saying he will repay me, etc. I started another thread where I mention a documented loan to him for $75,000. I have sent two separate demand letters. One for the $75,000 documented loan which he officially altogether denied ever happened until I forwarded the emails asking for the money, acknowledging receipt and the bank transfer slip. The second letter, he insisted they were gifts and that we were domestic partners even though we were together less than two years and less than 50% of that time together as we live in different states. We had no joint accounts. He never paid any of my bills or bought anything for me. I've decided to combine the debts and go to district court instead, as his denial of the $75,000 demonstrates what bad faith he has acted in. Do I need to do another letter of demand, combining these two, or can I just file now, as he has responded? I initially thought I would take two separate actions in Magistrates Court, but I really want to move on this and I also want the bald-faced lie about the $75,000 in evidence. In regards to the series of loans, I always referred to them as funds in the bank transactions, as I did the $75,000 loan. Nowhere have I ever referred to them as gifts. How likely is it that the court will see them as gifts? Well before our relationship ended, he was telling me he had this wealth of funds and a rental house and we had many email arguments (spanning about 15 months) about how he should access those to repay me. It turns out there were no funds and no rental house. All lies.