Breastfeeding counseling is an essential public health tool in postpartum maternal and infant health. In this study, we aimed to explore the relationship between the frequency of postpartum breastfeeding counseling and the type of feeding outcome at six months. The study design was an analytical, cross-sectional study on mothers of 6-24-month-old children living in Riyadh, Saudi Arabia. We conducted an analysis with descriptive statistics as well as logistic regression models. The findings from our study can be summarized in the following points: First, only 31.9% of the women in our study received postnatal breastfeeding counseling in the first six months after delivery, with the majority receiving fewer than four sessions. Second, there seemed to be a drop in exclusive breastfeeding with time: from 35.3% in the first two months to 29.7% in the second two months and then 20.7% in the final two months. Third, previous exclusive breastfeeding increased the odds of exclusive breastfeeding in the proceeding delivery. Finally, exposure to one or more postnatal breastfeeding counseling sessions increased the odds of exclusive or predominant breastfeeding in the first six months. This study helps to guide decision makers in planning maternal child health services and relevant community-based efforts.