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Evan KimmeyEvan Kimmey 

I'm trying to create a field dependency for a picklist that is depedent on a specific stage being selected on a closed lost opportunity, but when setting up the controlling field the option to select the second picklist is greyed out still.

To expand on this, when we mark an opp as Closed Lost, there are two fields Primary & Secondary Loss reason (both have same picklist options). One of the options is "Product Gap" which should then open another picklist called "Product Gap Area" that offers a more specific breakdown of the product gap along with a free text field to further expand if need be. The goal is to have this "Product Gap Area" & "Product Gap Details" appear when Product Gap is selected as Primary or Secondary loss reason. 
VinayVinay (Salesforce Developers) 
Can you share screenshot?

Meanwhile, check field dependency between if you have already created one also check lov access if you have any record type enabled.

Thanks,
Evan KimmeyEvan Kimmey
User-added image

I am able to get it for the first Primary reason however I am struggling with the "Product Gap Details" free text field populating underneath Product Gap Area and then duplicating this under the Secondary Loss Reason 
VinayVinay (Salesforce Developers) 
There might be any existing dependencies,  Can you check and review all existing dependencies on your object?
Evan KimmeyEvan Kimmey
There were not any existing dependencies upon further looking.
VinayVinay (Salesforce Developers) 
Without dependencies, there is no way it can popup. 

Is this a custom page?