“Wine Mom” culture has recently been popularized through social media, entertainment, and household products. Although numerous popular editorials and blogs scrutinize the behaviors associated with wine mom culture, little academic research has systemically investigated the topic. Thus, the current study uses semi-structured interviews (N = 22) and a phronetic iterative approach to explore how cis-gendered mothers—the targeted population of these messages—make sense of sarcastic “wine mom” messages, which can potentially trivialize or glamourize alcohol use and misuse. Sensemaking theory broadly informs how mothers interpret and are influenced by the wine mom messages (WMM) they see on artifacts scattered throughout store shelves or in people’s homes—such as signs, dish towels, or clothing. We build a taxonomy outlining the range with which cis-gendered mothers interpret WMM and explore their accounts and rationalizations of how WMM messages have effects on the social, psychological, and physical health of mothers.