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Answer: Because this is a joke and not a practical case, we do not have to analyze all of the potentially impactful details. I guess what makes the story funny is the implication that Shimon only thought of paying at that time and place because he hoped that the loss of the holdup would fall on Reuven. Apparently, though, the circumstances are more important than the intention.

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Rabbi Daniel Mann
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Mode of payment: If the borrower has available cash, he must pay with cash, but if he does not have cash, he can give the lender movable objects of the borrower’s choice (Shulchan Aruch, CM 101:1-2). The lender can delay repayment to wait for a time at which the borrower will have cash to give (ibid. 4). If payment is in real estate, average quality land is the basic standard (see ibid. 102:1). This element is not the issue in your case.
Timing of payment: The time that the debt is due is primarily for the benefit of the borrower, i.e., the lender cannot demand return of the money before the time set. Therefore, if the borrower wants to pay early, he has the right to do so (ibid. 74:2). However, since it is somewhat suspicious that one wants to pay early, if there are signs that the early payment may cause a loss to the lender, the lender can refuse to receive the money at that time (ibid.). Some examples are when the currency of payment is soon to be devalued or the tax collector is about to appraise taxes based on money on hand (ibid.). When the time to pay has come, we are to assume that the time of payment is fair for all, and we will not readily allow the lender to refuse to receive it then (ibid.). However, if it can be demonstrated that there is a significant and immediate disadvantage to receiving it then, it is likely that the lender can refuse (see S’ma ad loc. 5; Shach ad loc. 10). We then treat that timing like the following scenario regarding place.
Place of payment: The mishna (Bava Kama 118a) rules that if one borrowed money from his counterpart in an inhabited area, the borrower cannot force the lender to accept payment in a desert, because of the lender’s expected difficulty to preserve that which he received (Rashi ad loc.). If the borrower wants to return the loan to the lender in an inhabited area, but the borrower will have to go through a desert to get home, he may return it if it is on time but not if it is early (Shulchan Aruch, CM 74:1). The Aruch Hashulchan (ad loc. 1) says that in that case, the theft danger of going through the desert is minimal because he can arrange to go with a protected caravan. This indicates that that the important thing is not the place’s geographic category but the question whether the payment will be safe there.
Your case is a mix between a bad time and a bad place. In other words, the place may be fine except when this robber is there and the time may be fine in almost any place, but the combination of the two makes it a damaging time/place, at which Reuven does not have to accept payment. To conclude with a joke with a hint of halachic insight, we might suggest to Reuven to respond: "I would be happy to receive payment from you … in just a moment. As soon as our new friend (i.e., the thug) finishes his business, give me the money."

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