The literature on homelessness tends to focus on risk factors in people's social and personal lives that contribute to their situation of being without a permanent home. Alternatively, the following describes innate factors of intimate relationships that contribute to a situation of homelessness for men and women. We conducted interviews with 61 people experiencing homelessness in Calgary, Alberta, Canada. We were particularly interested in documenting with greater specificity their perceptions of their individual pathways to and from homelessness. Three themes emerged from the data describing the intersection between respondents’ intimate relationships and their situation of homelessness: (1) relationship breakdown; (2) the role and impact of having intimate partners during a period of homelessness; and (3) the nature of the intimate relationship and its impact on housing. The data suggest that aspects of intimate relationships should be considered by social service agencies when addressing a person's situation of homelessness.