Yesterday I received his message with a regular request to extend the deadline
That's a good sign, hopefully he'll come back and make things right.
I noticed you had not left a review on his trust wall that you had giving him this loan. I would assume that DarkStar_ was not aware of the loan he had received from you when he funded the second one in October. I wonder if he would have done so if he had been aware of your loan.
I don't want to tell you how to run your business, but it would be considerate to other lenders to leave a neutral review on the borrowers' trust wall.