This study addresses the similarities and differences in fatherhood across two generations, relying on the experiences of fathers and their sons. Twenty representative father and son dyads were selected from a larger sample of participants in a longitudinal study examining the leaving home transition in Israel. The fathers and their sons were interviewed about their attachment relationships using the Adult Attachment Interview. Fathers were also interviewed about their parenting via the Parenting Representations Interview–Adolescence. Transcripts of the interviews were analyzed using a qualitative phenomenological approach. Four central themes of intergenerational transmission, mostly reflecting differences rather than similarities across the two generations, were identified: from poverty and shortage to indulgence, from strictness and respect to permissiveness, from precocious maturity to normative development, and from distance to intimacy and closeness. Fathers appear to want to provide their sons with experiences that they missed as children. They appear to be successful in these endeavors, yet surprised by some of the unforeseen outcomes, such as their sons being spoiled and manipulative.