Over the past few decades, dual-career families have become widespread. As a result, managing the two most important domains—work and family has become difficult due to interference of the characteristics of work into family (WFC) and family into work (WFC). Research on this issue is very much rampant in Western countries; however, there are very few in the Indian setting. This study makes an attempt to study how WRC and FRC are related to WFC and FWC as well as the bi-directional nature of Work-Family conflict (W–F Conflict) among Engineering college teachers, a profession largely ignored even in the Western setting. Data were collected using a questionnaire and the sample size was 230. Confirmatory factor analysis was run to test the fitness of the measurement model. The structural model was tested using structural equation modeling and all the indices supported the fitness of the model. Regression weights indicate that work role characteristics and FWC are related to WFC, and family role characteristics are unrelated to FWC. The results of the study are discussed, and implications are provided, emphasizing the urgent need for more research in the Indian context.