Re: Planning holidays, dates etc
I'm lucky to be married to the planner of all planners. I'm a planner, too, so you can imagine what our calendar looks like. And yeah, we have months planned in advance!
My suggestion would be, pick 1-3 things that occur at least monthly in frequency. Odo and I do dance lessons every other weekend, we have season tickets to the symphony (one concert a month), season tickets to a local arts program (again once a month), agility training with our dogs one evening a week. We also have memberships to art museums. He can't travel on planes so we make the most of local events. We both work crazy hours and I'm working an extra 25-30 hrs a week on my masters classes, so our schedule is packed but balanced.
We go out to eat before the symphony, so it's like a monthly date.
Planning ad hoc doesn't really work for us. We can be spontaneous if necessary but if it's in the calendar, we can consider it time already booked and uninterruptable.
"If you deliberately plan on being less than you are capable of being, then I warn you that you'll be unhappy for the rest of your life."
~ Abraham Maslow