My boyfriend from Israel was planning on moving to the states to live with me. He brought about $10,000 here last time he came. He is now back in Israel and we decided he was not going to move here. How do I send him his money? Will it bring up red flags with the IRS if I wire it to his bank from mine?
Bank-to-Bank wire transfer would be the best option. Dollar is going up nowadays, so if he brought the money not so long ago he might even earn the cost of the transfers back through the difference of the exchange rates.
Re the IRS - they don't care. Same goes to the Israeli Tax Authority. What you and your friend need to show, if asked, is the paper trail. I.e.: if he brought you the $10K in cash - that may be an issue unless he kept all the receipts for getting it. But for such a low amount you can always resort to claiming it is a gift from you, in this case.