Introduction: The importance of helping pregnant women maintain a healthy lifestyle and prevent excessive gestational weight gain is well recognized, but pregnant women do not always perceive communication about body weight as respectful or helpful. Furthermore, fear of inducing shame or guilt can prohibit some midwives from talking about body weight, especially if the woman has obesity. We aimed to explore what women of reproductive age with obesity regard to be the most important and relevant aspects when discussing gestational weight management. Methods: Qualitative interview study using focus groups and individual semi-structured interviews with 17 women of reproductive age (19–39 y) with obesity. Thematic analysis was used to analyze the data. Results: We identified three themes: 1) Importance of obtaining vital medical information; 2) A wish to feel understood and treated with respect; 3) Midwives’ approach is crucial in sensitive key situations, which include bringing up the subject of body weight, weighing, providing weight-related information, coaching lifestyle modification, dealing with emotional reactions and ending a conversation. Conclusions: A majority of the interviewed women wished to receive information about risks about obesity and gestational weight gain, and recommendations on weight management. However, the risk of midwives offending someone by raising the topic may be increased if the pregnant woman believe that gestational weight gain is uncontrollable by the individual. Also, several situations during maternity care meetings can be stigmatizing and make women less receptive to advice or support. Women suggest that a good working alliance is likely to be achieved if midwives have knowledge about the causes of obesity, take interest in the patients’ background, have a non-judgmental approach and refrain from giving unsolicited advice.