I had a friend who was in school and I was always paying for his things. They went from small things such as meals at McDonald's to concert tickets and tickets for haunted houses. We ended up dating, within the time span of the four months I spent roughly 1,500 on him. I later found out he was getting money from his father and could have easily paid for everything. He told me he would pay me back for it most of the time. Is there any way I can get my money back?
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Not really. Unless you can show that there was an intent for you to have the money repaid (basically - a written loan agreement), no court will accept your claim.
This is one of the situations you can see frequently on "Judge Judy" and such, and the decision is always the same: unless there's a written (or you convince the judge about a verbal) agreement that it is a loan - it is a gift.

littleadv
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1-1 for any reference to a reality TV show. :) – JTP - Apologise to Monica Jan 31 '14 at 12:33
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1@joe while a reality tv show, "Judge Judy" is a real legal procedure with binding legal consequences. The parties are really in dispute, and the judge's decision is a real judgement (although arbitrage and not court judgement). – littleadv Jan 31 '14 at 21:38
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Even if a camera were in a real courtroom, that's 'reality TV.' There is a direct correlation between financial success and watching RT. See the work of Tom Corley, http://richhabits.net (of course the -1 was kidding, I voted up your good answer) – JTP - Apologise to Monica Feb 01 '14 at 13:30
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@Joe not arguing about it being reality TV, just saying that it shows the legal precedent very clearly. – littleadv Feb 01 '14 at 20:28