re = /(?<!\d)([.,!?])(?![.,!?\d])|\s{2,}/
str = 'Hello my friend.There should be a space after sentence periods and commas, but that should not apply to 40.381,32 numbers.'
subst = '$1 '
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