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Question does it say DLC installed in the upper corner if not don't worry it happened to me just do this 👇🏽

(Before u continue make sure ur DLC and the base game file has been extracted/unzipped)

(Window & Linux): Unfortunately I do not have Mac so if it's Mac sorry I can't be of help

Step 1. Locate the DLC

Step 2.(This one is crucial) Double click the DLC

Step 3. Once you've locate "14 Nights With You" Right click on it and press copy or however u usually copy files

Step 4. Head to the base game and click on that

Step 5. Locate the "game" file and click on that

Step 6. Right click or whatever u do to usually paste the "14 Nights With you" in there

Step 7. Once that done load up the game like you usually do and it should say the DLC is installed in the upper right corner of your screen