It’s 2025. Internet of things has taken of, and both machines have joined humans on the Web and in society. What do they do, how do we cope, and more importantly, how did we end up here? User experience has a major peak in importance: digital devices are everywhere, users are utterly diverse, and technology is getting highly advanced. Inventing better ways to let people interact with such technology has been the challenge of the 21st century. UX expectations are through the roof: children grow up as digital natives and think any thing is science. However, that is not all. The user spectrum has some new participants: machines. The rise of digital assistants introduce new challenges about how to deal with these newcomers. But how are we handling the next-gen AI-driven machine players, as they are the real digital natives. In this talk, we go over interesting use cases, positions and developments on AI. Furthermore, we touch on some technical and ethical fallacies in existing systems such as IBM Watson or self-driving cars. Finally, we illustrate future prospects and raise some challenging ethical questions.