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How far can I go just piling them up before it becomes gibberish?

友達たちは、のびのび 話して 歩いて ビールを飲んで 物事を考えて 歩いた

Is that something a Japanese person would actually say?

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    There are two 歩く and that feels strange to me. 「友達たちは、のびのび話したり、ビールを飲んだり、ときどき考え事をしたりしながら歩いていた」 would be natural. – naruto Jan 6 at 2:36
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Technically you can go on forever and it won't be gibberish. That said if you overdo it, it might make you seem like an inexperienced writer.

Young school children do this often (e.g. 「昨日は動物園に行って、ヤギを見て、うさぎを見て、お弁当を食べて、そしたらはなちゃんが勝手にライオンの方にいったので注意して、まさみ先生もいました」)

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