This chapter focuses on the evidence for the association between gestational weight gain and postpartum weight retention among obese women, as well as the association between obesity and lack of breastfeeding, and how these associations are potentially interrelated to cause further disease in obese women. Overweight and obese women are less likely to initiate breastfeeding and more likely to prematurely stop breastfeeding compared to their normal weight counterparts. There is currently little investigation of the interrelationships between obesity, pregnancy, and chronic disease. Risks of hypertensive disorders are highest among obese women who maintained or increased their BMI between pregnancies. Maternal obesity is also associated with later development of type 2 diabetes mellitus (T2DM/pre-T2DM) and heart disease (CHD)/pre-CHD. The current literature suggests that maternal obesity has many long-term health consequences for the mother; however, the degree to which pregnancy contributes to these outcomes is uncertain.