It seems that you are new to this, so a few words of advice.
-buddy passes are more of a curse then a benefit in my opinion
-have them start early in the day, so they have back up flights
-make sure you warn them that they might not get on the flight and that their behavior reflects upon you.
-a lot of times they might be able to find a guaranteed flight on priceline.com for just a little more
-avoid connecting flights the less flights the better
good luck