This mixed-method Writing-for-wellbeing pilot study used a pre-post-follow-up design with 20 adults in two groups (10 in a bereaved group and 10 in a non-death/living losses group) to assess the feasibility, acceptability, and potential efficacy of a longitudinal writing intervention in helping participants to work through their grief. Participants completed measures of prolonged grief, adaptive coping, anxiety and depression, and meaning reconstruction. The qualitative analysis was based on a satisfaction questionnaire that included open-ended questions. The intervention was well-received, safe, and personally valuable. The bereaved group reported reductions in symptoms of anxiety, depression, and prolonged grief, and increases in adaptive meaning, help seeking, and spiritual support. The living losses group reported a decrease in help seeking.