Learning exercise - original exercise was to build a program that would reverse the word order of a string. I extended it by preserving the location of the punctuation (minus apostrophes) in the sentences to make the reversed strings a little more readable / interesting. First attempt - a little sloppy, but it works!

reversopunctuator.rb

puts "Please enter a sentence."
user_input = gets.chomp

array = user_input.downcase.split(' ')

punct_indices = {}

array.each do |x|
  contains_punct = /[[:punct:]&&[^']]/ =~ x
  if contains_punct
    punct_indices[array.index(x)] = x[contains_punct]
    y = x.sub(/[[:punct:]]/, '')
    array[array.index(x)] = y
  end
end

reversed = array.reverse

if !punct_indices.empty?
  punct_indices.each {|key, value| reversed[key] << value }
end

reversed[0].capitalize!

print reversed.join(' ')
puts

Almost each action that you have separated by spaces could be a method. Then the action sequence written out, to perform what you need to have done.

Of course, that prompt routine, should probably be a routine already, and stored in a file, to be used many times.