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I skimmed documentation of Python after people told me it was fundametally similar to Lisp. My conclusion is that that is not so. When you start Lisp, it does `read', `eval', and `print', all of which are missing in Python.

Could someone explain what he means? (Did Python not have a repl when he wrote that?)

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Python's read doesn't return a s-expression, nor does its print take one; they just use strings. It's eval likewise takes a string. The part missing that lisp has is the inspectable data structure containing an arbitrary parse tree and function result.

I am curious, would Ruby be a good fit in this case? With its irb and all.

No, Ruby's implementation of it's interactive mode is similar to Python's - not via data structures, but via strings.

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