Last fall we did WDW with another couple and it worked well. An old friend of mine married a widow who was/is a Disney fanatic. Randy was in his late 50s when they married 5 or 6 years ago, IIRC. He had never been to Disney, but went several times with her and her family after the marriage and became instantly hooked. He's an engineer and is fascinated with how it all works.
Anyway, over the past several years we talked about each other's trips, and last year I suggested we try to coordinate a trip together. His wife thought it a good idea, so we started planning.
We got together over a meal and decided which places to eat and which parks to visit, etc. They're DVC members, so we stayed in different hotels. They only booked 4 days, while we booked 8. On the four days we were together, we spent a good part of the day together, but not all, and dined one meal together each day.
It worked out quite nicely - my wife and Randy's wife Kathy got on well - and Randy & I have a lot of common interests. It was a little different than when it's just me and wife, but we made some good memories - so much so that we're contemplating doing the same thing thsi fall at DLR/DCA. Randy's never been there and Kathy hasn't been since 1976.
It probably helped that 3 of the 4 of us are DIS fanatics. My wife likes WDW/DLR/DCA, but she would not meet the definition of fanatic.