As innovative way to express grief, social media posts about the deceased have become fairly common. However, few studies examined grief photos commonly posted. The purpose of the present study was to examine such pictures, as well as the motivation and reactions of those who posted, among Italians and Americans. Surveys were sent to both Italian and U.S. participants. The U.S. group yielded 262 responses (Mean age = 22 years; 81% female), the Italian yielded 51 (Mean age = 32. Several key issues emerged, such as the need to receive empathic support from other users, the desire to maintain continuing bonds, the wish to remember the deceased, and the desire to share beauty and symbolic pictures. The images were analyzed using content analysis. Both samples posted photos to remember and to enhance their posts. A strong preference for pictures with a positive emotional connotation appeared, depicting the deceased in a conjoint appearance with the participant. Results suggest that imagery used for the expression of grief in social media sites, an “iconography of grief,” is a popular means of expression for grievers.