Within the last several years, new types of media for interpersonal communication have been developed. This means that the personal media environment of current students at German Gymnasien is different to that of former students. In turn, it is assumed that mediated interpersonal communication with friends has changed as well. This study seeks to highlight and reason these changes through an investigation of former and current Gymnasium students’ communicative practices via personal media. Although these two groups are both proclaimed to be “digital natives”, a difference may exist, as different forms of communication media were available to them when they grew up. It seems therefore accurate to refer to them as “early digital natives” and “late digital natives” depending on when they were born in the course of the developments. Insights from twelve interviews with former and current students were analysed by the means of grounded theory. The results show that the late digital natives’ mediated interpersonal communication differs considerably as it is more concentrated on one medium and characterised by a continuous flow of communication. These results, among others, are discussed and explained with the help of the media capabilities, the medial-conceptional distinction, and the niche theory. Corresponding communicative changes are argued and brief comments are made on the concepts of friendship and digital natives. The study concludes that the personal media environment has a considerable but not exclusive impact on the students’ mediated interpersonal communication and testifies to how quickly communicative changes can take place.