We need one of 2 things. Either:
x Add messages with older date to Skype conversation
or
x Fake an app that looks like Skype and we can open the conversation there
The idea is to show that me and person x had a conversation 2 years ago.
I have been developing software professionally for 5 years. I can easily make a knock off Skype for you and I believe I can change the dates on a Skype conversation if an image is all you need. I strongly encourage you to message me.
I can do it in Delphi but it will be an offline application, it isn't a real life application, on? So, you need to specify what skype windows you need.