They were a cute duo.
Imagine all of the great scenes we would have gotten if he had taken her to some of his favorite places (and vice-versa) and if they had tried to get each other interested in their favorite hobbies. The fact that they are so uniquely different makes comedy gold.
Betting on the ponies
bargain shopping
He would actually listen eagerly to her rants and comment on them. He was so in awe of her.
I can just picture him giving her a standing ovation at that play.