Go on the date, stay in the moment, and just be you. e that laid back, careless, and forever young self and things will go fine.
As for the dream...My take is that it represent you feel subconsciously like you are helping your wife deal with her emotional baggage. The lack of overall feeling I would take as you are not emotionally invested in her emotional journey other than frustration it has taken so long. So overall I would say a pretty good dream and look into how your subconscious is viewing what is happening in reality.
