How to build a website with user login, timelines with text based posts and user submitted images

I am new to web development. I have some knowledge of wordpress and I am learning Django at the moment. The reason I took up Django is because I wanted to create a website as mentioned in the title, and I thought that is the right way of doing it.

What I want is: A site where user can login and have very basic timelines. The user can submit a drawing (let's say) in response to another's wish. This matching of a user with a wish would be random and will be stored in a database. The timeline should have a particular user's wishes or the drawings submitted.

This is the basic idea, how should I go about creating it. I have one to two months for this project to be completed (I did not want to rush any learning). If anybody can just give me an outline of the things I will have to learn and implement in order to achieving the said target.