Depends on who it is really. I lent my entire PS1 Final Fantasy collection to my mother-in-law 4 or so years ago. I know where they are, I know they are being taken care of so I don't have a problem lending her games.
I will my brother too, but that is after he and I got into it because I loaned him Final Fantasy Anthology and Chronicles. A friend of his convinced him to loan them to him and "the friend" denies it ever happened. Note this person used to be a friend of mine too, until I caught him stealing from me. So there is a rule, no matter who it is, don't loan them to anybody else, period. Other than that one incident he's been really good with them.
Anybody else, hell no. I used too. Lost a few games and had some that were worth quite a bit at the time get really beat up. I didn't realize they were worth anything at the time. That one is on me though.