This case study describes a region‐wide, multi‐sectoral, and whole‐of‐community stakeholder engagement approach for addressing sea level rise (SLR) and flooding. This approach was implemented through a university‐led community engagement event, the Hampton Roads Resilient Region Reality Check (H4RC), which allowed an examination of its effectiveness as a mechanism for capturing community‐wide perceptions regarding SLR, flooding, and associated risks; engaging stakeholders in discussion within and across different groups; and assessing community willingness to address flooding and SLR. The results show that the event helped participants broaden their perspectives and understanding of flooding and SLR. In an approach that called for participants to engage in social learning across social networks, the event had some effect on individual efficacy. However, there was little impact on participants' already‐established perception that the region does not possess significant willingness to take action.