Seems like a pretty basic necessity
Also, besides downloading watch faces in the Connect store, the onboard watch faces can be customized to have 4 data fields and you choose which of the many fields to display, date being one of them.
Of course it can display the date, I always have the date displayed on my watch face. Do you have the watch?
Depends on the watch face.
Find a watch face that displays the information that you need.
I use the Crystal watch face and it displays the date.