re = /(".*?"|(?<!\\)'.*?(?<!\\)')(*SKIP)(*FAIL)|\?/
str = 'This is my test ?
I "stole ""?"" it from s/o"
I "stole ? it from s/o"
I "stole \'?\' it from s/o"
I \'stole "?" it from s/o\'
"?" look like it works pretty well ?
\'this is a question mark - ?\'
\'this is a double-quoted question mark - "?"\' ?
\'this is a single-quoted question mark - \\\'?\\\'\' ?
\'this is a ? badger\\\'s question mark ? where is the monkey\\\'s\\\'\' ?'
subst = 'plant'
result = str.gsub(re, subst)
# Print the result of the substitution
puts result
Please keep in mind that these code samples are automatically generated and are not guaranteed to work. If you find any syntax errors, feel free to submit a bug report. For a full regex reference for Ruby, please visit: http://ruby-doc.org/core-2.2.0/Regexp.html