The expectations and roles associated with fatherhood have been changing at an ever-increasing pace over the last several decades, from sole economic provider to engaged and nurturing caretaker and equal partner. Alongside this shifting landscape, men also face changes in individual, household and political contexts that influence their ability to fulfill these new roles and responsibilities. Despite strong desires to be there for their families, men express difficulty in overcoming the various barriers to their success in these efforts. This dissertation explores several of the key determinants and outcomes involved in relationship duration, father well-being, and the uptake of paid parental leave after the transition to parenthood. Data for the first two chapters come from the Future of Families and Child Wellbeing Survey (FFCWS), and the third chapter relies on data from the European Union Labor Force Survey (EU-LFS). Chapter one examines whether fathers’ instrumental support (or “being there”) for their families can protect against the union destabilizing effects of low-income and employment. Findings suggest that while instrumental support leads to longer relationship duration, it cannot fully compensate for poor economic provision or violation of gendered expectations regarding the division of labor. The second chapter examines the effects of child support debt on fathers’ economic, physical and mental well-being. Fathers with child support arrears are more likely to experience poor physical health, depression, and material hardship such as difficulty paying bills, food insecurity, and inadequate access to healthcare. The third chapter is a cross-national study that examines how paid parental leave generosity influences mothers’ and fathers’ use and duration of leave in the years following the transition to parenthood. Results indicate that more generous parental leave is associated with the higher likelihood and duration of fathers’ leave taking, but not mothers, and generosity was particularly important for lower-income fathers. Together these chapters highlight the barriers men face in attaining the level of involvement they desire with their families, and the mechanisms and policies involved that can be targeted to improve outcomes over several domains that can have lasting effects for fathers, mothers, and their children.