def convert(text) text.lines.map do |line| if line =~ /^\s*\*\s(.*)/ line = "<li>#{convert($1)}</li>\n" end line.gsub!(/\*([^\*]*)\*/, '<strong>\1</strong>') line end.join end puts convert(DATA) __END__ *this is bold* *yup * this is a list * foo *bold* * here