Amidst the contrasting debates between the loosening caste-based prohibitions on marriage and the tenacity of endogamous marriages, which is explicit in cases of ‘honour’ killings, this chapter focuses on how caste mediates in romantic relationships and marriages. It examines the routes inter-caste couples take to gain social validation of their amorous relationship and the response meted out to them by the family and kin members. It shifts attention from the transformation observed in marriage practices of urban middle-class-upper castes to the lower middle-class and castes. Examining inter-caste marriages defying the line of “purity” provides insights into the intricate and reluctant negotiations between modern ethos and traditional values in urban areas.