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Well, interesting question. You are within one year of the statute of limitations running on this matter which would bar him from suing you for the money (the statute of limitations on this is 6 years). That said, since he did not cash the check and since you were not out the money then, I would recommend going ahead and paying him the cash now. However, I would have him sign a piece of paper which has a sentence or two, like this....
"I hereby acknowledge the receipt of $150 from (your name). The payment is made in cash and the debt is settled as payment has been made in full. I will no longer seek payment on this debt and covenant not to cash any check previously received from (state your name) relative to this debt."
You both then sign it and date it. Give him a copy and you keep a copy of the release of debt.
This way, the debt is paid, your relationship is salvaged and he is contractually barred from cashing the check.
Let me know if you have any other questions or comments.
Best wishes going forward!