The worst was probably a flight from Chicago to California after a business trip. The flight was fine, but I had a cold and the pressure from the descent and landing made me feel like my head was going to explode. The pain was so bad that I thought I was going to pass out. I was alone on the flight except for two co-workers who had upgraded to first class while I was back in coach. I almost rang for the flight attendant at one point, but I toughed it out until we landed and the pain went away.
Another flight wasn't bad so much as highly annoying! We were flying from California to Florida to drop our son off to college. The emotional part of that was hard enough. But when we got on the plane, I discovered that my seatback TV was broken! No way was I flying for that long without a TV! I mentioned it to the flight attendant and he said, "Yes, that one is is broken, but I can reseat you after everyone is on-board." He came later and moved me to an exit row aisle seat with no one in the middle! It was awesome since my moving also left the middle seat between my adult sons open. I turned on the TV and settled in to relax for the flight, only to realize the family near me was going to be a challenge!
There was a young couple in front of me with a baby (who didn't turn out to be a problem at all!). Across the aisle was grandma and grandpa, who I figured out were the mom's parents. The baby's dad sat in his window seat without moving for the entire flight. He slept, watched TV, wore his headphones and basically seemed to tune out the fact that his wife and child even existed. Mom, grandma and grandpa took turns holding the baby, but grandma and grandpa kept arguing over not getting equal time! At one point the baby fell asleep with grandma and the mom stood in the aisle next to her for nearly an hour while the baby slept. It was kind of ridiculous. Then grandpa decided it was his turn and started trying to pull the baby out of grandma's arms. A low-key argument ensured, but I couldn't understand their language so I can only guess what they were saying. Then grandma took the baby to the empty exit row behind me and mom followed. They laid the baby in the middle seat between them until a flight attendant came along and told them they couldn't have the baby in an exit row and to return to their seats. So mom let grandpa have the baby and sat in her seat in front of me. Next thing I knew, mom tossed her rather long hair over the seat back and it completely covered my TV screen! I waited for a minute to see if she would shift positions, but no, she put her head back like she wanted to sleep. I leaned forward and tapped her on the arm and said, "Excuse me. I can't see my TV with your hair on it." She said OK and quickly moved it. The rest of the flight consisted of the mom getting up to look at or stand next to the baby when her parents had her. Mom also trekked up and down the aisle like every 30 minutes to get water for herself and her parents. I'm sure the flight attendants enjoyed her visits to their station in the back. They brought their own lunches which didn't smell very nice in an enclosed airplane. My older son came up and said, "Hey! You got extra legroom! Want to trade seats?" I almost took him up on it. But my older son has autism and sometimes has strong reactions to annoying people who make noise and invade his space. I didn't want to leave him in that situation, so I said no, you're better of back there with your brother.
We took many more trips to Florida after that to visit our son at school. Luckily, I never had a flight as annoying as that one!