since the AD column in the sheet "typed " cannot be formatted to compare it to a date, the only thing i can advice you to do is to change column AD data in which date is entered correctly, to a piece of text that can be compared to the text in typed sheet: in an empty column, say AF, enter this formula: =TEXT(AD1;"mmm-yy"); copy this formula down to your row range; then click on column letter AF to select the entire column AF , click on AD1, and paste only values( paste special- only values). In this moment, AD1 column can be compared... look at sample attached..
Hope this fits you