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. A close ...

Student loans can be debilitating for young people. This man paid off his girlfriend’s student loans with his winnings, but that wasn’t enough for her. She also wanted him to pay for her sister’s ...

A man is seeking advice on Reddit after he paid off his girlfriend's student loan debt as a birthday present, despite her wishes that he didn't. Money is a continued issue between the two of them, as ...

Sometimes you don’t really know someone until money is involved. Money can really show you someone’s true colors. In today’s story, one man paid off his girlfriend’s student loans. But that wasn’t ...