Required + Sender field isn't working?

We have a simple template that goes out every week.  There are only three fields:

1) The anticipated date of use (completed by me, the Sender)

2 & 3) The recipicient's signature and the date signed

I cannot for the life of me figure out how to add a date.  I've added a date field in Adobe forms, but I'm never prompted to complete it.

I got more sophisticated and added a date field in Adobe eSign, tagged as both "required" and "Sender" - and I'm still never prompted to complete it.  

Do I have to add myself as a recipient on the document in order to get a chance to add the current date?

I'm going in circles!