I remember trying Ruby out years ago and being turned off by a REPL I couldn't understand (Python's REPL was excellent) and a lot of Perlisms in the syntax (e.g: sigil support, regexps built-into syntax). Going back from indentation based syntax was also a minus.

More recently, when I looked at Ruby, I was somewhat turned off by the use of code blocks as a building block, rather than lexically scoped functions. I find functions simpler to compose and reason about than code-blocks, and found it peculiar that functions were expressed on top of blocks.