Let me just start by saying, that overall I think I am a very charitable person; not because I feel like I am obligated to be but because I have good friends and family and so why wouldn't I want to help them. Well recently I started dating this guy. Met him at a downtown hotspot in my city; gave him my number started talking when out twice and subsequently became an item (although it was never officially stated--he just assumed and I went along with it). One day we decided to rent a car, but because I'm not a legalized driver yet ( I know I'm lagging at age 22) I lent him the money to put on his card for the deposit since he didn't have enough. It ended up being like 350 dollars and he's like don't worry you get the deposit money back (which I knew). Now, the pool of money that I withdrew from was for school tuition, some of which I saved up and the rest my parents gave to me. Anyhow I was expecting it back so I wasn't as worried. Then later that same day he told me that he needed to pick up his prescription and that it was going to be 160 dollars or so. I believed him because he seemed genuine about it and if it's a medical need how can I say no. He said he would pay me back by the end of the night cause it was his birthday. Long story short he didn't pay me back that night and I found myself begging to school to extend a deadline. I pretty much told him that he needed to pay me back asap and he's like I cant, I don't have money. Blah blah blah. He was like we never agreed that I would pay you back. I was like are you serious? Like really? Now, he's like its my fault I shouldn't have lent him money and he blocked my calls and messages. I know I can take him to small claims but I know it will cost money and if that's the case I want to do it right. Im somewhat knowledgeable on the proceeds of the lawsuit but only because Ive googled it. I wish to seek further legal counsel so I know I'll win... besides having western union receipts and screen shots of his texts on my phone. Im really tired of people taking advantage of my kindness.

Faith in people is all very good. Trust in someone you barely know is foolish. Trust is for people you KNOW WELL. You meet some guy in a bar and next thing you know you dish out $510 in one day. Saying 'I know I get the deposit back' doesn't even make sense when you didn't put down the deposit, he did - using your money. He thinks you are made of money because you get some from your parents and because you are too easy. As for small claims, sure you can win (maybe, where's your proof?), and if you win, you are awarded the fee too, but it doesn't mean he will pay. Getting paid takes more and more court filings, and even then you might not get the money.

Faith in people is all very good. Trust in someone you barely know is foolish. Trust is for people you KNOW WELL. You meet some guy in a bar and next thing you know you dish out $510 in one day. Saying 'I know I get the deposit back' doesn't even make sense when you didn't put down the deposit, he did - using your money. He thinks you are made of money because you get some from your parents and because you are too easy. As for small claims, sure you can win (maybe, where's your proof?), and if you win, you are awarded the fee too, but it doesn't mean he will pay. Getting paid takes more and more court filings, and even then you might not get the money.

Yeah I realize I didn't know him very well. But on his behalf, if he was going to go through such great lengths to take money from me then why do I have all his information. I many be easy but the thing is I've lent money to people (co-workers) and former friends in the past and they always paid me back. Like I said I have proof of him saying he was going to get the money back from me, then he said he was never going to. Its all in texts. I also have the western union receipts with his information.

There's no logic in a statement that a person has lent money to people in the past and been paid back and therefore it should happen with the next borrower.
There isn't much logic in your claim that 'having his information' means that he will repay you.
Many of us have been through this - I'm out thousands from one person (who died broke).
If you feel that your texts are proof enough for small claims, then file. If he fails to show, you win by default. It still doesn't mean he will pay. If he does show up chances are good that you will win, but it will depend on the judge and how each of you acts. They handle 'gift vs loan' cases all day long.

I am sorry, he was a con man and they are more believable, I don't understand he he was renting the car, you still could have used you card for the deposit, I do it all the time for one of my sons when they are in town. Next how was he going to pay all of this back, sorry his birth day?

This is a common con on women men pick up at bars.

Yes you sue him, but, when you win, how are you going to get his money. You win, you now have a judgement against him, so what bank account are you going to garnish, Do you know where he works, to garnish it ?

Winning is simple, collecting the money is hard.

But you appear in court, tell the judge the truth, show him what reciepts you have, copies form credit card or bank statements.