Building on the extensive literature highlighting the key role digital and social media play in the lives of LGBTQ people, this article adds a generational perspective by studying the importance of the internet and social media for different generations of men who have sex with men (MSM). Focusing on issues of identity exploration and the search for information as well as social connection, two periods are distinguished: the time of sexual identity exploration, and the present. Based on a mixed-method design, a survey ( n = 684) was used to measure the perceived importance of online platforms (particularly Facebook, Instagram, Tumblr, YouTube, and TikTok), while in-depth interviews ( n = 80) helped to better understand how digital media are embedded in the context of everyday life and society. The results show an ever-shifting range of digital media which subsequent generations come across at different times in their lives, fulfilling similar needs with the tools available at that time. This study contributes to the literature by adopting a life course approach to the study of media use among MSM of various generations, which allows to disentangle the respective roles of age and generation.