I had one like that...she booked a window seat and couldn't figure out why I didn't want to sit next to her.

That said, I am the organizer for work trips. Most of my team rarely travel by air outside of work and even then it is 1-2X annually. I just tell them when and where to meet. (Although I have convinced a few to enroll in TSA Pre-Check.) On the personal side, I have organized a number of road trips for away football games. Usually one of us is responsible for the hotel, one of us is responsible for transportation, and one of us is responsible for the 'big' dinner. The rule is if you don't want to plan, you can't complain (or don't go). It's been successful formula over the years.