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 I am a fellow player  that needs very specific directions, so I hope that this helps you and those like me. (This is for windows only, I do not have Mac. I also put this VNG into a custom folder.) Sorry, this will be long. If how much space this takes up is not appreciated, please tell me and I can delete it (or I will try to figure out how)

Before DLC:

1. Go to the most recent demo update (currently 5.5) and download it (you have the option to donate, but you also have the option to "just take me to downloads" to.. well, download). It is highly, HIGHLY recommended to delete ANY prior old files/content from any old versions of the game. Do so, please. This may be making you crash.

2. Click the downloads once finished, or go to your files and see your most recently downloaded ( should appear as "14dayswithyou-pc-5.5" or similar) with the "Type" column as "Compressed (zipped)".

3. Double click it. Then, click "14 Days With You" to see the folder's contents.

4. Amongst other elements, you will see "14DaysWithYou", and in the "Type" column to the right it will say "Application". Double Click "14DaysWithYou". 

5. You will be given the option to "Extract All", click it. IF you get a pop up of a warning, under the shown text you will have the option to "see more info" or something. Click that, then click the option "run anyway".

6. Once all opened/downloaded, now you have "14dayswithyou-pc-5.5 " with the "Type" as  "File folder" column to the right, AND the original file we downloaded: the "Application" type. This just came from it lol. To play the demo, double click  "14dayswithyou-pc-5.5 ", then "14 Days With You", and finally, the little heart icon with "14DaysWithYou". But if you want to add the DLC then,

DLC:

1. Go to DLC, and pay through any options. I did PayPal and did not have to link my account, just a email of my choice. Download once given option to.

2. Now in your most recent downloads as "14nightswithyou-paid" with the "Type" as "Compressed(zipped)". Click once, and the verrrrrry top of your Files window, you will see the option to "Extract". Do it, its fun!

3. Fun as in now you will have "14nightswithyou-paid" with the "Type" as "File folder" in your recently downloaded.. I think. Just look, there!

4. Now, move "14nightswithyou-paid" ("Type" as "File folder") oovvverrr to our familiar friend "14dayswithyou-pc-5.5" with the "Type" as "File folder". To move it, hold click and drag the paid version onto the day 5.5 demo folder, then release you click.

5. Double click "14dayswithyou-pc-5.5"  (Type: "File Folder"), and it opens to the elements "14 Days With You" and the folder you just dragged into it: "14nightswithyou-paid".

6. Drag "14nightswithyou-paid" onto "14 Days With You" and release. Double click "14 Days With You" to open, and you will see the "14nightswithyou-paid" folder you just dropped in along with a lot of other elements. This page should have the Pink Heart Icon as an element!

7. Now! Drag "14nightswithyou-paid" onto the element/folder "game" with the "Type" as "File folder". Now it is in there! You can now click the Pink Heart Icon with the name "14DaysWithYou" to play. Hopefully, this has worked and I have not flubbed anything up in my instructions as these are the steps I took. Again, let me know if I should delete it. It may take me awhile to respond.