It was 8th grade and my grandmother had just passed away. Her funeral was in Florida and my dad decided to directly fly into New Orleans and drive over since it'd end up being cheaper and we'd be able to see the French Quarter and Battleship Bay driving through before we had to be in Florida for the funeral.
We were flying out of Seattle and had a flight at 4 in the morning so we'd be able to land around 11am-12 EST(with time conversions). As we check in, we're told the flight is delayed a little bit(30 minutes) so we have some extra time. Not 5 minutes later we're again told the flight is delayed and will be taking off around 6. Not the worst thing in the world, but when we're told we cannot take off until 10 we're all on edge. My mom is on the verge of tears and exhausted, my dad is demanding some sort of refund from the help desk at some guy not prepared to deal with a 6'4' 250 pound man this early, my older brother is knocked out laying against out carryons and I'm trying to stay awake so I can fall asleep on the plane - praying we can maybe board something sooner.
After we board begin flying, I fall asleep soon after and wake up while still on the flight. I ask my dad how much time had passed and he said just over 4 so we'll probably be landing soon. Another hour passes and we end up landing in WASHINGTON, DC. Turns out that they couldn't fly into New Orleans for whatever reason so we had to make a connecting flight there where we had ANOTHER delay happen, flying out of DC at about 6 pm Eastern Time. About 5 hours after we were expected to land in New Orleans.
Luckily, nothing ELSE happens on our flight down but we land and the rental car my dad was supposed to get apparently is faulty, and we WOULD'VE had to wait if the teller didn't see that every one of us was about to snap, but we made it to our hotel and managed to fall asleep fairly well. Rest of the trip went as well as it could've gone but I still keep that memory of flying in the back of my mind so I can always say "Well it's not that trip at least".