During the Second World War, Allied-occupied Italy became the setting for a wide range of intimate encounters between local women and the occupiers, especially American soldiers. These relationships – ranging from romantic and consensual to transactional and coercive – reflected complex interactions with perceived ‘otherness’ and exposed tensions around race, gender, and power. US authorities, concerned about its social, cultural, and political implications, monitored ‘fraternisation’ closely. This article explores these dynamics by examining US Army marriage regulations and oral history interviews with Italian women who married American soldiers. Women’s experiences – shaped by region, class, and individual circumstance – represent a spectrum ranging from disillusionment to long-term partnership. These narratives offer a complex portrait of gender relations under occupation, revealing how military policy also intersected with and shaped the everyday lives of women during occupation.