I covered the entrance fees ($250) for another golfer to play with me in a tournament and he promised to pay it back within 2-4 weeks,been 4 months

Asked on May 23rd, 2017 on Contracts - Florida
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He has agreed he owes the money via text messages which I have saved as evidence and has a million seemingly good excuses why he could not find a way to get me the money, should I send him a demand for payment and how much time is standard? Should I take him to small claims court and what are my chances of winning?
Answered on May 24th, 2017 at 6:13 AM
At that value - its a $250.00 learning lesson on not loaning what you can't walk away from and tolearn this person is of law character. 
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