Both speakers in the examples sound unnatural. The human doesn't know what to talk about and seems to have little confidence. The robot says things that only mostly make sense and draws on, saying ultimately very little. "How's the winter stuff?" e.g. is not a sentence a person would say. I might say "How are you dealing with the snow?" or "Are you looking forward to winter?," but not "How's the winter stuff?" And there's just so many examples like this. Also, I'm not convinced that this "human-like" conversation with filler words and interruptions and pauses is actually what anyone wants, especially in absence of a face to interpret or a real human being to understand behind it. Even if it worked perfectly, it would feel uncanny and artificial because I know the person isn't real.