In this article, the authors describe how they "accidentally" developed an informal yet powerful way for them to connect with each other, debrief, deconstruct, detox, and demystify their respective new jobs as a department chair and college dean. They found a very natural way to connect with each other as women leaders. As two women negotiating difficult times in new leadership roles, they were in the unique position of having shared a context, of having constructed the same department together. They called their informal meetings, "Wine and Whine," and met monthly to engage in their "therapy sessions" over dinner and a glass of wine. Through these casual meetings, they used their common experiences to problem solve collaboratively, but more importantly, they offered each other that ephemeral, spiritual, and emotional support that they now understand is a critical ingredient of women supporting women.