Through the description of two high risk unplanned pregnancy cases and the subsequent interview of the patients, a few years after delivery, this article focuses on the following issues: 1. The importance of a planned pregnancy in a woman with diabetes or other chronic disease; 2. The ethical role of counselling and how it should not be influenced by the ethical belief of the obstetrician; 3. The legal aspect related to the knowledge and qualifications of the obstetrician in the management of a high-risk pregnancy to improve both maternal and fetal outcomes. Here, two cases of complicated type 1 diabetes in women with unplanned pregnancies and the importance of counselling in high-risk pregnancy are presented.