The person willing to lend again has noticed what happened the first time.

A second loan is not a repeat of the first; it is a verdict on it. Whether something came back, in what state, and whether anyone had to ask are all quietly recorded, even by people who would never mention it. Willingness is the evidence that the record is good.

If you borrowed something recently, return it early and in better condition than required. If you are the one being asked again by somebody who has been careless before, you are allowed to lend something smaller or to say no without a reason.