in reply to Regexp match start or end

> But being AI, it can be unpredictable!

And because of this I'd rather stick with separated, simple rules which can be easily maintained.

Better expect more trouble to come.

> with the single word "Perfect"

Your logic is flawed though, this

$reply !~ /^perfect/i

will not only match (well reject) "single words" at the beginning.

Cheers Rolf
(addicted to the Perl Programming Language :)
see Wikisyntax for the Monastery