Fascination with Italy has been going on for centuries and is still prevailing in the literary perspectives of the British writers. While the writing styles show symptoms of change in the course of the selected last half of the twentieth century, the writers also vary in their observations with overarching discourses shifting the vast network of signs. Thereby, apart from portraying the various beauties of the Italian sun, landscape, religion, politics, art and music during the twentieth century, British writers have also started to reflect on another aspect of their cultural contact with Italians, marriage which becomes more complicated in the relational network of intercultural marriages – a Briton marrying an Italian or vice versa. This article particularly focuses on intercultural marriages in Eric Linklater’s Private Angelo (1946), Jonathan Keates’ The Strangers’ Gallery (1987) and Tim Parks’ Cara Massimina (1995), Europa (1997) and Destiny (1999), with the aim of discussing the kind of confrontation marriage with an Italian creates from the British male writers’ perspective.