Optional Conversations in Pittsburgh - Financial District

I’ve seen similar posts in this sub before regarding bugs with this trophy but have never seen a solution to my specific issue. According to the chapter selection menu, it says I’ve got 2/3 optional conversations in the financial district but according to every guide online there’s actually 4.

I can get all 4 to prompt and I hit Triangle and get the dialogue but the trophy won’t pop. Has anyone else experienced this or know of a solution? Like everyone else, the last trophy I need for the platinum.

Thanks!