You should ask him what he intends to do about the situation. If he can't pay you now but acknowledges the debt, ask him whether he will sign a promissory note providing terms of repayment he can live with. If he says he won't pay, file a small claims action.
This answer does not constitue legal advice, nor does it creat an attorney/client relationship. If you are seeking legal advice upon which you intend to rely, you should hire competent cousel familiar with this area of the law in your locale.
Mr. Boss gives very practical advise about trying to get a writing now that he can live with, and succinctly gives you the only alternative: small claims court. One can sue on an oral contract.
The above is general legal and business analysis. It is not "legal advice" but analysis, and different lawyers may analyse this matter differently, especially if there are additional facts not reflected in the question. I am not your attorney until retained by a written retainer agreement signed by both of us. I am only licensed in California. See also avvo.com terms and conditions item 9, incorporated as if it was reprinted here.
In what form was the money loaned? Was it in cash or was there a check? If check, did you put in the notes that this was a loan or refer to the emails? Those notations can help prove the loan to a court. Until you demand payment or a payment is due, the statute of limitations probably will not begin, so you may have more time to consider your court options. For instance, even if this is an oral agreement which has a two-year statute of limitations, the period to file a suit would not begin until the borrower breached the payment terms. If no payment is due and the borrower has not stated an intention to not repay, then the two year period has not begun.
Robert Stempler (please see DISCLAIMER below)
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