Blurred work-family boundaries have become more prevalent due to various demographic, structural, and institutional transformations, such as the rise in dual-earner families, technological advancements, and cultural norms surrounding work, gender, and family. According to role theory, blurred work-family boundaries can create conflict and tension between one’s role as a parent and as a worker, which may, in turn, lead to a decline in well-being. Mothers may be at greater risk than fathers of diminished well-being resulting from blurred work-family boundaries due to gendered caregiving expectations. In this chapter, I examine the associations between various measures of blurred work-family boundaries and subjective well-being among employed mothers and fathers. I use the time diaries in the National Couples’ Health and Time Study to examine how happy, stressed, and engaged mothers and fathers feel while performing paid work and childcare over their time diary days. My results show that multitasking paid work and childcare is particularly stressful for mothers. Paid work interruptions associated with childcare is also detrimental to mothers’ stress. In contrast, for fathers, neither multitasking nor paid work interruptions is associated with stress.