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Just make sure you file with PayPal within 45 days. As long as you didn't send as a gift, they should be helpful in trying to recover the funds from his account. If the funds are gone, they may still refund you. If not, you have to decide whether or not the consequences of filing a chargeback with your card are worth risking PayPal closing your account (for the record, I filed a chargeback once because it had been 46 days and they didn't close my account after I got refunded).
Two very basic rules of PayPal:
1) NEVER EVER EVER pay as a gift. Don't do it. Pay the fees, it's worth the price of admission to have the guarantee.
2) Don't pay with your bank account (EVER). Set up a free online checking account (Simple, Ally, etc) and link that to receive payouts, but never pay with a bank account since you can't really do a chargeback in case of emergency. If someone ever files a dispute against you, PayPal can lock down your bank account. You won't be able to go to the ATM or use your debit card until it's resolved (up to 45 days).
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