The rapid expansion of mobile dating applications has reshaped how intimate relationships are initiated while creating new contexts for romance fraud. This study examines how romance fraud unfolds within India’s digital dating environment through a qualitative analysis of 35 media-reported cases from 2020 to 2025. Anchored primarily in Space Transition Theory (STT) and complemented by Routine Activities Theory (RAT), the analysis examines transitions from digitally mediated communication to offline encounters, with attention to offender strategies, target characteristics, and situational conditions. The findings identify a recurring interactional pattern in which offenders initiate contact on dating platforms, engage in emotional grooming to establish trust, and subsequently arrange in-person meetings. Offline encounters alter the dynamics of interaction by introducing greater immediacy and, in some cases, reducing opportunities for disengagement. These encounters were associated with outcomes ranging from financial loss to coercion, extortion, and physical harm. The findings suggest that romance fraud is a cross-contextual process in which offending evolves across interconnected online and offline environments rather than within cyberspace alone. Hybrid guardianship is used as an analytical lens to examine how digital, social, and environmental forms of protection intersect and change across stages of the fraud process. Given the limitations of media-based data, interpretations focus on observable offender strategies and reported situational contexts rather than inferred offender motivations or definitive claims about guardianship effectiveness. The study contributes to research on cyber-enabled crime by illustrating how romance fraud unfolds at the digital–physical interface in India.