I am to the point I never lend anything. If you get it back, you are going to have to go get it. They won't bring it back. It was enough trouble (for them) going after it, in the first place.
A signed copy of a book. Never to be seen again, nor the 'friend.' I give, don't lend, when I can do that. It makes everything easier.
I lent out the electric guitar I had built as a student when I went to Luthiery School... Never did see it again.
out of print books i never got back. although that's kind of understandable in one case as it was more of their being taken then intending to lend and the person wasn't allowed to come back, having made themselves persona non grata anywhere near where i lived. not just to me but to half the people who lived there who had lent cell phones and the use of their bathrooms.
in any case, out of print books and periodicals, are the jewels i most regret ever "lending" (though as many have been lost by having to leave behind)