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I made the mistake of lending out my Diablo 2: Lord of Destruction back in 7th or 8th grade. The guy I gave it to claimed that the disc got stuck in his CD-ROM and he couldn't retrieve it, to later on claim he had lost it. I got another copy, but ever lent out anything to this one ever again.

Otherwise, I've been incredibly anal about getting my games back from various people I had them lent out to.