One component in the generational experience strongly related to media is the intimate and often passionate relation that is developed towards media technologies and content from one’s formative youth period: musical genres and stars, as well as reproduction technologies such as the vinyl record, music cassette tapes, comics and other now dead media forms. Passion, however, is a dialectic concept that not only refers to the joyful desire and intense emotional engagement of cherished objects but also includes its dialectic opposite in the form of pain and suffering. This passion, it is argued in the article, is activated by the nostalgic relationships to past media experiences, the bittersweet remembrances of media habits connected to earlier life phases of one’s own. Taking its point of departure in generational theory of Mannheim and others, this article analyses a series of focus group interviews with Swedish and Estonian media users tentatively belonging to four different generations. Based on the analysis of these interviews, it is suggested that passion and nostalgia are produced, first, in relation to old technologies, second, in relation to childhood memories and, third, at the limits of shared intergenerational experience, that is, at the moment when one realises that one’s own experiences of past media forms cannot be shared by younger generations, and especially one’s own children.