Our advice columnists have heard it all over the years—so we’re diving into the Dear Prudence archives to share classic letters with our readers. Submit your own questions to Prudie here .

Dear Prudence,

A close friend, “Sam,” and his girlfriend, “Emily,” are doing something truly terrible. She has a lot of student debt to pay off, so they have come up with a plan.

She will date and marry someone rich, and he will pay off her student loans, and then she will break up with him to be with Sam after a few years. All the while they will be cheating on Mr. Rich together. Sam told me that he is not looking for advice. But he still wants to talk to me about this plan and how it is affecting him a lot. I do not want to talk about this. I think it is despicable to trick someone into ma

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