Is its name 'Bridle Apprentice'? If so, you're saying hail and bridle, $text=~/bridle/i checks the whole string for "bridle" and $text=~/hail/i checks the whole string, too. Due to them both being if conditionals it checks each of them individually rather than checking sequentially and stops when it find one. Maybe try this:
Code:
sub EVENT_SAY {
if($text=~/hail/i) {
quest::say("Hail $class. Do you seek to earn a [bridle]");
} elsif($text=~/bridle/i) {
quest::say("I suspect, as most of us these days,that you are a bit low on platinum? Well no need to worry! Simply handle a...well,[situation] for me");
} elsif($text=~/situation/i) {
quest::say("I have a high intolerance for the Tuffien these days. If you would be willing to bring me back one of their hides I will be willing to [reward] you");
} elsif($text=~/reward/i) {
quest::say("Bring me back any color hide and I will give you the corresponding bridle");
}
}