In my opinion, Javascript would be the best option to begin because you can mess with it with the chrome's DevTools. In Javascript, there are nothing called alloc and free so you dont need to worry about memory at the first place. Next, there are nothing called entry point also. Even a single line of javascript are considered valid. For example, window.alert("Hello words");
As you learn deeper into the javascript, you will learn more about the Object-Oriented Programming (OOP) stuffs such as classes. Then you will have an issue on type-casting. However, the experience you gain when dealing with such issues are very helpful in future programming and in progress of learning strong-typed programming such as C and C++.
If you want to write some desktop application, the next language that you should learn will be either C or C++. C++ is basically a extension toward the C with the OOP stuffs. In learning these language, you will learn more about the native system apis, byte ordering and memory management. Additionally, you will learn about the ASCII and Wide Char Text if you deal with Windows API.
Hope my opinion helps