We're not super close, but we are coworker. He started off by asking me for $350 to pay a car loan. I was already a bit uncomfortable with it since we don't know each other super well, but others have said that he's good for it. After I sent it on cash app, he turned around and asked me to send it again because he apparently took it out on the wrong card and had to wait a few days to be get it back. Annoying, but an honest mistake so I did it again believing I'd get at least half of it back pretty quickly. He did send me the first $350 back the next day, but ended up needing it again because he got charged twice for the car payment. So whatever, we're back to where we were. Now he's asking me for another $800 for some tickets he apparently has. I didn't really want to, but he set out a plan to actually pay me back, which made sense. I did it under the agreement that I'd at least get the original $350 reimbursement in a couple days to prove that he's serious about paying me back. (It was done on a Thursday, and weekends don't count as a business day) After sending it, he again asks me to send it a second time because now his bank is withholding it as they investigate the double charge on the car payment. He's worried that if he doesn't pay for the tickets, he could be arrested for it. I know he's a good person and I don't believe that he's trying to scam me or anything, but I'm very reluctant to send him any more. I also need to save the rest of my money for when I try to move out. I feel like I've definitely helped him enough, but I also don't want to see him possibly get arrested for unpaid tickets. He's saying that he'll have a good $1350 of the $2300 that he would owe me by Wednesday, which would be fine but I'm just not sure at this point