Purpose of Review: Initial conversations about weight with patients are important to set the tone for future dialogue and management of obesity. There is often reluctance in raising the topic of overweight or obesity in consultations. We aimed to evaluate literature to discover the perceived barriers to optimal discussion about weight status and preferred weight-based terminology for adults, adolescents and parents of younger children. Recent Findings: Fear of offending patients, insufficient training and lack of knowledge of referral pathways were identified as factors hindering healthcare professionals’ ability to discuss weight with patients. Neutral terms, such as ‘weight’, were preferred by patients, with ‘fat’ and ‘obese’ viewed as undesirable and stigmatising words. Summary: There is a need for greater support and provision of specific training, including education on communicating weight status, for those involved in the management of obesity. More research is necessary to assess the impact of interventions to improve initial discussions with patients about weight. © 2021, The Author(s).