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uh yeah so i had this issue too and what fixed it for me was that i had the package contents of a date with death in one finder window (newly downloaded, havent opened the game) and my downloads page in another and i just forcibly dragged and dropped it into the file where the archive file was and the dlc showed up in my game afterwards so mayb u cld try that?

Ouuu, I wish I had seen this before buying/moving it all to steam because I got sooo frustrated, I just played it through steam so that everything could update to the game without having to manually move files ughhh but for future reference, thank you for this !!