In Sweden adults with major and sustainable disabilities can be granted publicly financed support in the form of personal assistance after assessment and decision-making in accordance with government rules. The purpose of the present study was to explore more deeply the encounters in close care relations between personal assistants and disabled persons of working age, as well as the prerequisites for and obstacles to the success of such encounters, this from the perspective of the personal assistants. Thirty-two personal assistants (22- to 55-year old) who worked for 32 persons with serious neurological diseases living at home were interviewed. The transcribed unstructured interviews were qualitatively analysed using latent content analysis. The analyses resulted in five main themes: Perceptive awareness, Entering into the other’s role, Mutuality, Handling the relationship and Personal difficulties facing the assistant. These themes illustrated that a prerequisite for the encounter’s being meaningful is that the assistant should be able to observe and understand the unique needs of the disabled person. The assistant must furthermore be able to put herself/himself into the other person’s position. It is also important that the personal chemistry between the assistant and the disabled person should be good. Being able to share feelings and interests with the functionally impaired person provides the assistant with positive emotional confirmation of a good relationship. A distressing dilemma the assistant faces is that of distinguishing between the working relationship and the personal friendship. In this borderline area are found experiences, feelings and events that the assistant may view as negative or even unacceptable. This study contributes to the understanding of the complexity underlying the daily community care of disabled persons with an extensive need for care and assistance.