This 8-month research explores the paradoxical feelings of "guilt" and "pleasure" and their impact on women's psyches. The study examines the 'guilt' women associate with consumption and indulgence, and how "guilty pleasure" affects their perceptions of health and femininity. I interviewed 15 local businesswomen in Providence and Boston from the wine, food, and wellness industries. These industries provide products that women find both pleasurable and guilt-inducing, with wellness often seen as a virtuous alternative. Each interviewee shared her unique perspective on guilty pleasures, exploring their meanings and the reasons behind the associated guilt. The findings reveal numerous social, cultural, and historical factors influencing their experiences, with few women reporting no guilt about indulging in food. This project offers insights into food, health, and sociocultural dynamics from a feminine perspective.