Well here is a 2 step solution. It still may have a problem if you encounter lines with 2 or more 'it' in them. Its called regex greediness. See greediness . I leave you some work to fix the possible greediness issue. :-)

#!/usr/bin/perl
use strict;
use warnings;

while (<DATA>) {
  if (  $_ =~ m/([?.,]$)/){ 
        # print " matching first criteria $_"; 
        
        #now check for 'it', using capture parenthesis
        #for the text before and after 'it' 
        if (  $_ =~ m/(.*)it(.*)/ ){        
         print "$2\n";  # the second capture parenthesis  
       }
        
  }; 
        
}
    
__DATA__

4 score, and 7 years ago?
our ? forefathers came,
upon it -- a continent.
it was it was it ? foo?
.bar bazz    
__END__
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