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Learning with the Lender
Reuven borrowed money from Shimon, and Shimon used the opportunity to inquire if Reuven would want to setup a Havruta session with him. Is this an issue of Ribbit?
The Shulhan Aruch writes that a borrower may not tutor the lender, nor the lender’s son, unless he had been doing so previously. Some Poskim write that this is forbidden even if the lender has other Havruta opportunities.
It is possible, however, that this only applies to tutoring, which is usually done for money or as a favor, and not to learning Havruta-style in Yeshiva, which is normally done without payment.
However, if he definitely would have not selected him as a Havruta it would not be permitted.
It is important to note that where Shimon clearly expresses his desire to study with Reuven as a condition for the loan, it would be forbidden under all circumstances. Hence, it is important to avoid mentioning this, even in casual connection to the loan (“Okay, I’ll lend you money, but please learn with me…”).