Health experts have suggested that we face an epidemic of loneliness in the westernised world. But what do we mean by loneliness? In this article I explore what leads to states of chronic loneliness, the language people use to describe it—if they can, and why it is that some people savour solitude and others fear it. Here my thesis is that the former have benign internal objects to draw on, and this opens space for creativity and the imagination whereas the latter experience an inner void. I talk about the early experiences that contribute to feeling lonely, even when people are around, and to an inability to internalise supportive others. The article also includes a section on the connections between loneliness and shame. At the end I discuss what a therapeutic relationship, and in particular one grounded in a deep understanding of what being alone means to the therapist, can offer so that people suffering acute aloneness can move from fearing being on their own to valuing the transitional space of having time to themselves.