That condition would check if the last order date is the same as the order that started the workflow. So if it’s true you know they haven’t purchased any product. But I suspect you want something that is specific to the SKU. For example, they could’ve purchased any product.
Doing that latter thing is more complicated and depends on your store. For example, how would you know that a sample is related to full size product? Are they different variants of the same product? Does one always have “sample” in a product attribute or a tag?