re = /((?:s?he(?: i|')s|(?:you|they|we)(?: a|')re|I(?: a|')m).{1,20})\b(Fan)(s?)\b/i
str = 'He\'s the bigest fan I know.
I am a huge fan of his.
I know she has lots of fans in his club
I was cold and turned on the fan
An air conditioner is better than 2 fans at cooling.'
subst = '\\1\\2atic\\3'
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