One way to answer this is to recast the question into something else (which has Calvinism presumed), and then address it that way. Or not.
I would say that the father’s principles dictated that if his son wanted to leave with the money, then his son has already left, in his heart, and that it would be wrong (and potentially dangerous) to hold him back, against his will. But does permitting him to do this, make the father complicit, in any way, with his son’s actions? On the one hand, if the father had put a stop to the whole thing, then the thieves and prostitutes might never have gotten their hands on the money, and misspent it, however they willed. So the father bore some responsibility, since it was his money that was ultimately flowing into the wrong hands, but it should also be pointed out, that the father never wanted for that to happen. All the father did was to consent, allow and permit the son to have his way, not that he caused his son’s poor choices, in any way. But I think that what Calvinists do is that they first assume Calvinism, and then proceed accordingly. So that way, God has a decree, number 1, and all is determined. Check. Now if God should “permit” something, then this “permission” must necessarily be consistent with the decree. Check. Now if God does permit something, then He has “decreed to permit it,” and thus even His permission is the “outworking of the decree,” and so the resulting choices also can trace their way back to the decree. So in this way, everything is decree-driven, in the Calvinist’s mind. Since this is the foundational presumption, certain “proofs” will be needed to support it, and thus questions arise, such as, “If God knew what people’s choices would be, then He must necessarily have determined those choices.” But the logic doesn’t follow, as it still remains to be proven, that God’s knowledge in any way causes people’s choices. Then it is asked, “Why did God create people (and certain angels), knowing what they will choose?” Well that’s God’s prerogative, to create beings that will be faced with choices, but simply being given choices, does not require that God determine what they will make of their choices. For instance, God created good angels. With their choices, 1/3 fell. God’s permission didn’t make their choice for them, no more than His permission made the 2/3’s remain loyal. In terms of humanity, why did God allow people to be born, that He knew would ultimately reject Him and perish? Again, this question springs from the necessity to provide a proof-text for the “immutable decree,” since that is the essential foundation for any Calvinist. Nevertheless, the answer is addressed in the parable of the “Wheat and the Tares,” as people are interconnected, and God chooses to wait until the end, to sort it out. As a practical illustration, imagine if God knew that a particular father would reject Him, and perish. But what if God also knew that the son or daughter of that father, would instead accept Christ and receive eternal life? By preventing the birth of the father, the hypothetical child will never be born. So, in this way, people are interconnected. However, back to the point of divine permission, it has long been the protest of Arminians, and non-Calvinists, that Calvinism is logically inconsistent with “divine permission,” and I feel that this criticism is absolutely fair and reasonable, and Calvinism lacks a sufficient answer, other than to relegate everything to an eternal decree, which is the world-view of every Calvinist.