[Victoria]

In November 2004, I entered into an agreement with the gentleman that I was dating at that time to run a horse stable.
I was to secure the property and he would manage the farm business. In consideration of this agreement, we looked at multiple farm properties together. After I purchased the agreed upon farm, my "partner/farm manager" failed to relocate as agreed upon. I had paid some legal fees, vehicle repairs and other minor debts for my partner in preparation for his relocation over the same time frame. Now, I'm stuck with a huge mortgage and no help with the business that he was supposed to be managing in return for my assistance with his debts. Can I sue for breach of contract?? The combined total debts paid on his behalf were $23,000. I could break some individual payments into amounts for Virginia's small claims court, but not the largest debt. Cashier checks and personal checks were used; will they be proof enough?? I have two receipts for cash that he received from me that are signed. He has promised to do work on the property, but he never shows up to actually do the work. I have only received $100 over the past 6 months towards his debt!?

[aaron]

It isn't clear how strong a case you would have, given that it appears that many (perhaps most) of the expenses were not directly business-related, and your ex- may well contend first that they were gifts, and second that your motivation for suing is not the business but is instead anger over the break-up. If you can get him to agree in writing that some or all of the amounts were in fact loans, and that he is obligated to repay you, you would be in a much stronger position to litigate your claim. Of course, I'm putting a worst-case spin on things - you know better than anybody here whether he would go to court and admit to owing a debt.