# line 36 text.split("#").first This will have trouble with a line like: tweet = "TOML is #awesomesauce" -- # line 43 array = $1.split(",").

# line 36 text.split("#").first This will have trouble with a line like: tweet = "TOML is #awesomesauce" -- # line 43 array = $1.split(",").map {|s| s.strip.gsub(/\"(.*)\"/, '\1')} You should recurse into coerce here, or you'll just lose types. (Also you're assuming arrays of strings.) array = $1.split(",").map {|s| coerce(s) } -- You're also not dealing with nested key groups. (eg. [servers.alpha]). -- That being said, naïve string parsing is a terrible way to build a new markup language implementation. It's the reason the Markdown landscape is such a mess[1]. What this really needed is a formal grammar. [1]: I actually tried to fixed that by writing a formal lexer & informal parser for Markdown in a side-project of mine[2]. It's not quite there yet, because for practicality reasons I wrote my own parser instead of a formal AST-generating parser. https://gist.github.com/kballenegger/29dabe4b6e762ee221df https://gist.github.com/kballenegger/29dabe4b6e762ee221df [2]: http://getmacchiato.com http://getmacchiato.com