re = /\b(\S)[^'\s]*('?)\S*\b/m
str = 'I\'m a little teapot, short and stout.
Here is my handle, here is my spout.
When I get all steamed up - hear me shout!
Tip me over and pour me out. '
subst = '$1$2'
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