In this thesis I investigate different meanings of singleness as understood by women who are alone. Using data from interviews with 30 women aged 30 to 60 years, I examine how women work with a single identity in a social context that is changing rapidly. I focus on identity and self-representation through looking at discourse, and the discursive and conversational moves made by participants. My project is interdisciplinary in nature, benefiting from developments in sociology and psychology in an applied social science approach. My analysis draws on critical discursive psychology, and makes additional use of traditions in narrative analysis and conversation analysis. Examination of how participants talked about themselves and singleness shows linked but distinctive forms of 'trouble'. The culturally available and familiar resources for understanding singleness are highly polarised, and participants demonstrated rhetorical work in weaving their ways through the extreme contrasts of a denigrated or an empowered identity. The cultural context incorporates new representations of singleness while continuing to offer continuity with older, more devalued notions. I argue that these polarised ways of thinking create a troubled identity for single women. Telling the story of her life and relationships also presents trouble for the woman alone. The familiar and dominant cultural storylines of western society are of committed heterosexual relationships and ensuing family life. Such resources for telling a life story were at the same time useful and troublesome as participants positioned themselves in comparison with, and at times resisted the familiar storyline. Furthermore, representing themselves as possessing agency and having made choices in their lives was problematic for participants. I also focus in a more detailed way on some patterns of troubled interaction in the interview itself, and consider the relationship of interactions in the interview to broader issues of stigma and social exclusion.