Configurable List: Is it possible to set up conditions based on the widget?

In example #2 - I want the MM/YYYY (date field) to show up if only the check box for each item is selected.  I am unable to find a way to use any type of conditional formatting in the for a ‘configurable list’.  

Unfortunately, it's not possible to set up conditions based on the widget or with fields in the widget. 

As I can understand, you want to set up a condition to show a date field once a check box field is filled, but both fields are set up inside the Configurable List widget. 

Is my understanding correct? 

Please let us know, we will be glad to open a feature request for this.