Is it proper to return something– and then ask for mechilla in case something was damaged or is missing? Or is this a halachic problem? ( I am wondering because I thought I remember a halacha that in some cases it is not permitted to ask a question that the other person will feel obligated to say yes to)
Someone lent me a box of children’s clothing with many articles of clothing inside. I tried to gather all of the items together, but I am not certain if some of the items are missing (and have reason to think that some items might be missing). Can I return it to her saying that “I tried to return all of the items, but I am not sure if some are missing. So if anything is missing or damaged, are you mochel?”
You should return it and ask mechila, exactly as you wrote in your question.