The Riddle Game is not the best tool to draw the conclusion that the languages (or, better said, speech patterns) of Gollum and Bilbo were particularly ‘close’. The riddles were common to them both, but as written, they were almost certainly put down on paper as Bilbo knew them and not as Gollum actually spoke them. Writing his memoirs many years later, Bilbo likely could not remember exactly how Gollum had phrased his riddles, so he wrote them down in the form familiar to him.
Likewise, the rambling sing-song way that Gollum spoke in is not indicative of the way his people communicated. Gollum was clearly insane and very out of touch in a social sense. With no one to talk with but himself for 500 years, and hindered by the mental machinations of the Ring, it is doubtful his speech patterns much resembled those of his long-gone family.
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The Barrow-Wight
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