Of course don't mention this to your wife, but a couple things do;
1- You have mentioned many times that she is very impulsive. Not just in the "I like that dress so let's buy it" type impulse, but in a lot of areas.
2- She seems to lose focus quickly....Like so many of your conversations are unfinished. You two seem to do that a lot, almost like she loses focus on the conversation and moves on to her next focus item.
3- Hyper focus....Not as much, but a few times it has seemed she has become hyperfocused on one thing.
I may be wrong as it was just a thought, but communicating with an ADD person is a little bit different. Not bad, but just different.
As for the planning and date jar....good ideas, but I am getting the feeling your wife wants you take a bit of control. You make the plans and get things lined up.....What feels like a good activity for tomorrow? Then just do it.