Relations between grandmothers and their grandchildren following the loss of the son/father have not been studied to date. The present article focuses on this experience, as reflected in the stories of grandmothers (bereaved mothers) and spouses (widows) after the loss, and explores the perception of grandparenthood following the loss of the son/husband. Twenty semi-structured interviews were conducted with ten grandmothers (bereaved mothers) and spouses (widows) who were recruited as a convenience sample. Data were subjected to thematic analysis. The findings revealed three key patterns of the grandmother–grandchild relations, as perceived by the two groups of women. The patterns indicate complex relations between widows and bereaved mothers, which have implications for the access of the grandmothers to their grandchildren and for their perception of grandparenthood. The study sheds light on the patterns of relations in families that have lost the son/husband/father. The change in power balance between family members and the asymmetry in the family structure created by the absence of the son/husband affect grandparenthood relations. The study emphasises the role of the widows, as the middle generation, in shaping or mediating relationships following the loss. The findings stress the importance of clinical intervention with both the bereaved mothers and the widows.