use strict;
my $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.';
my $regex = qr/((?:s?he(?: i|')s|(?:you|they|we)(?: a|')re|I(?: a|')m).{1,20})\b(Fan)(s?)\b/ip;
my $subst = '\\1\\2atic\\3';
my $result = $str =~ s/$regex/$subst/rg;
print "The result of the substitution is' $result\n";
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 Perl, please visit: http://perldoc.perl.org/perlre.html