This podcast, suggesting a gentle wry smile in Dt 1:6 was inspired by a blog post from Rabbi Michal Shekel “Could it be possible to stay too long at the site of Revelation?”
There are also quotes from: Tigay, J. Deuteronomy. Jewish Publication Society, 1994, 8; and Rashi on Dt 1:6.
As well as Dt 1:6-7 I will also refer to Mark 9.
So, here’s the link to the audio: Humour in the Bible: Book 5 Deuteronomy