Taking photos of oneself and sharing them on social media or instant messaging apps is a practice haunted by shame. Although both media and popular wisdom view it as a simple exercise in narcissism and vanity, research into this practice shows contradictions, ambivalence, and tensions. Drawing on an empirical study carried out with young adults in Madrid, we explore the ambivalence, or “conflicting desires” as one interviewee put it, associated with affective and attention economies involved in this practice. Despite being a common, everyday activity, taking photos of oneself, seeing oneself in them, and sharing them generates mixed feelings, ranging from pleasure at seeing and playing around with one’s image, to estrangement and disquiet. We analyze how different kinds of shame are elicited. We also explore the time entanglement of both shame and the sharing of personal images online, in which memories of the past are intertwined with forms of continuity and discontinuity between the past and the present, and with the expectation of what will be remembered in the future.