We have a big list of "dates" and select based on seasonality, weather, what we want to eat, etc. We throw some randomness in there so its not boring. works well. In November, the resort hotels are cheap, and we visit them.
I am the whimsical person who has no problems coming up with ideas. My wife likes things nailed down, so that "communication issue" was an occasional problem early on. I try to make sure each date has three things: food, entertainment, and talking.
I never really thought about it. I usually just come up with an idea, suggest it and that's what we do. We are rather systematic though in our likes and dislikes.
My wife and I always vote on that.. she gets 2 votes and I get 1 vote