c:\@Work\Perl\monks>perl -wMstrict -le "use 5.010; ;; for my $string ( '\"my\" \"dog\"', '\"my\" \"dog shepherd\"', 'my dog', 'my \"dog shepherd\"', '\"my \"dog\"', 'my \"dog shepherd', ) { my $paired = qr{ \x22 [^\x22]* (?: \\. [^\x22]*)* \x22 }xms; my $unpaired = qr{ \x22 [^\x22]* \z }xms; ;; my $orphan = $string =~ m{ $paired (*SKIP) (*FAIL) | $unpaired }xms; print qq{'$string' }, $orphan ? 'INVALID' : 'valid'; } " '"my" "dog"' valid '"my" "dog shepherd"' valid 'my dog' valid 'my "dog shepherd"' valid '"my "dog"' INVALID 'my "dog shepherd' INVALID