What is the ruling on reclaiming a debt from someone to whom I lent money with the intention of its repayment when available, taking into account not embarrassing him, and is the money permissible if the debtor borrowed it to repay?

It is permissible to demand a debt from an affluent debtor. As for the one in hardship, he must be given respite, due to the Almighty's saying: "And if there is one in hardship, then grant him respite until a time of ease." There is no harm in demanding a debt from a debtor in hardship if the creditor is unaware of his difficulty. Granting respite to the one in hardship and overlooking his debt is a cause for Allah's forgiveness for His servant, and such a person will be among those whom Allah shades in His shade. For in the Hadith (definition): "A man used to lend money to people. He would tell his servant: 'If you come across someone in hardship, overlook his debt, so that Allah may overlook our sins.' The Prophet said: 'So he met Allah, and Allah overlooked his sins.'" And in the Hadith: "Whoever grants respite to one in hardship or waives his debt, Allah will shade him in His shade." And in the Hadith: "Whoever grants respite to one in hardship, he will have charity for every day, and whoever grants him respite after the due date, he will have the like of it in charity every day." It should be noted that it is not permissible to establish a relationship between a non-mahram (definition) man and a woman except within the limits of Sharia (definition).