My exboyfriend and I were only together for a short period. While we were together, I had tried to cash a payroll check for him out of my account (he didn't have his bank account set up at that point). He couldn't cash it because it was in his dad's name (yes, it was really his check, there was some confusion with the business, as he used to work under his dad and once his dad left, they didn't put the insurance in his name, so the check was in his dad's. His dad knew I was trying to cash it for him.) I ended up just pulling the money out of my account and giving him the check to give to his dad. His dad finally went to the bank with him and deposited the check into my ex's new account. I never got the money. He also built up over $500 on my credit card, plus other money I loaned him. All I want now is the amount the of the check and the credit card, which puts it at $1944.xx. He kept telling me he'd pay me back, the day we broke up, I told him I needed to start getting some of it back, this was almost 2 months ago. At this point, it's just a bunch of nonsense and now he is trying to tell me he paid me back and I'm crazy. I never saw a dime of it. When I asked him when he supposedly paid me back, he didn't answer. He is also holding onto some of my personal items I had at his house, a Keurig and 6 Redbox movies, which ended up costing me almost $200 because he never returned them. He has other small items but those are the only ones I want back. He has been telling me for months he would bring them up or give them to my friend that lives near him. None of this has happened. He is incredibly frustrating. All I want is what's mine. How do I get the ball rolling to start a civil suit?

First question... did you get any of this in writing from him acknowledging he owes the money and how much?

You will sue him in small claims court, but the issue is proving it is a loan, and not a gift, normally boyfriends and girlfriends give each other help on money, This is the issue, proving, that it was a loan, not a gift.