In the two cases discussed in this paper, we compare the development of a boy and a girl during the separation-individuation process. We have chosen two children, Charlie and Anna, who were faced with similar problems. From the very beginning each of their mothers had difficulties reading her child's cues and responding to them, and each found it difficult to be optimally available to her child as the separation-individuation process unfolded. Both mothers' difficulties were in part connected to their new baby's gender. Both Charlie and Anna followed by about 3 years a child of the opposite sex, and in both cases the presence of an older sibling interfered with the mother's relationship to the new baby. In particular, Charlie's mother had experienced the closeness with her first baby, a little girl, very intensely, and had to struggle with the