When in Live mode, items in a Sim's inventory cannot be dragged and dropped in order to place them. It will just stay in the inventory. The only way to work around this is to click the item and then ...
Ideas
Johnny Zest married Katrina Caliente. Before marrying, I put stuff in his inventory to bring with him in his new house. Now that he moved, stuff is locked in his inventory and cannot be dragged out.
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