Originally, it was just a kind wish for the journey.
These words were used in Russia to bid farewell to people embarking on long journeys, without any negative connotation. In the context of the eternal Russian mud, nothing could be better than wishing for a smooth and clean road, like a tablecloth.
In one of Ivan Aksakov's poems, there is a mention of a road that is "straight as an arrow, with a wide smoothness, like a tablecloth laid out." This original meaning of the phrase is recorded in Ozhegov's Explanatory Dictionary. However, it also notes that in modern language, its meaning has changed to the opposite: "An expression of indifference to someone's departure, as well as a wish to get lost anywhere."
This is not surprising, as polite formulas often undergo ironic reinterpretation. But not only they. Many other words and expressions, originally having a positive meaning, have become negative. For example, "to talk someone’s ear off" once meant a regular medical procedure, but now it is synonymous with deceit. Moritz Michelson's dictionary interprets this expression as "to persuade with ulterior motives." And the phrase "Keep your pockets wide!" still sounds like a call to action today in the mouth of some seed seller in the province, rather than a mockery.
