Is it illegal for a 19 year old female to Skype with a 14 year old male. She is not being provocative or anything and he messaged her first. They are simply just friends who talk about random stuff sports movies celebs... etc. Nothing inappropriate is being said.

There is nothing illegal about anyone calling, IMing, or otherwise talking to a anyone. As long as nothing illegal goes on in the communication it is fine.

However, since it is a minor, if you are told to end all contact by the minor's guardians and you do not do so, that could be illegal.

Now why do you ask?