Workplace emotions are intense and disruptive, so contagion becomes inevitable. With the presence of diverse groups of employees, from generational cohorts to genders, working side by side, workplace dynamics have become quite challenging. We study the factors leading to emotional contagion and its impact on the most prominent generations present today—Generation X and Y. Additionally, we also study the gender differences on emotional contagion at workplace. The factors were shortlisted via a comprehensive literature review. A qualitative research methodology has been used for deeper understanding of the topic. In-depth interviews with 62 respondents (34 from Generation Y: 16 males and 18 females; and 28 from Generation X: 15 males and 13 females) were used for data collection. Data analysis revealed that there were differences in the ways various factors affected emotional contagion for these two generations and on males and females. Based on the analysis, we have presented research propositions for quantitative validation which can be explored by future researchers.