ABSTRACT This study comprises in-depth qualitative analysis of transcribed audio recordings from therapy with Avoidant Personality Disorder (AvPD)-patients, with focus on the characteristics and challenges within the therapeutic relationship. The dataset comprises sixteen therapy sessions. The analysis employed Reflexive Thematic Analysisand yielded two themes: (1) Difficulties in conveying personal material and (2) How to get connected? The findings indicate that the patients struggled to share openly in sessions–often resulting in dialogues characterized by silence, lack of personal material, and a reduced sense of alliance. The silence seemed to represent a therapeutic challenge. Lack of observable ruptures made us hypothesize that the patients’ modus operandi was a detached mode. When the therapist made use of the “real relationship,” it seemed to affect the vitality and felt security of the patients. The findings indicate that these patients face difficulties expressing “a voice of their own,” posing a challenge in the relationship. To mitigate patients’ relational cautiousness and detachment, they may benefit from a therapist capable of scaffolding their efforts towards a strengthened agency and a sense of self. The risk of pseudo-alliance or subtle alliance ruptures, requires additional therapist attention and suggests that the relationship should be an explicit focus in therapy.