Self-compassion is a healthy way to interact with oneself in response to difficult situations. Interventions designed to increase self-compassion have focused on individuals writing self-compassionately about past negative events. It remains unclear if self-compassionate writing about anxiously anticipated events can help manage future-oriented distress. One population for whom this approach might prove beneficial are socially anxious people, for whom distress about the future is relevant. Study 1 explored whether describing anxiously anticipated events could elicit distress and whether self-compassionate writing was more effective than control writing in addressing such distress. Socially anxious participants were randomly assigned to write about an anticipated anxiety-provoking event (n = 236) or a neutral event (n = 50). The former group (n = 224) were then randomly assigned to write about that event again, in either a self-compassionate (n = 133) or neutral (n = 91) manner. Writing about the anxiety-provoking event proved effective at eliciting distress. Subsequent self-compassionate writing about the event increased state self-compassion, positive affect and determination to engage in the event. Study 2 evaluated whether writing about an anxiously anticipated task (i.e., the Trier Social Stress Test: TSST) in a self-compassionate manner would promote objective performance on the TSST and a subjective sense of success. Socially anxious university students (n = 85) completed the online study in three phases: 1) baseline self-report measures; 2) random assignment to self-compassionate writing (n =34), control writing (n = 26), or no writing (n = 25), then the TSST, and state self-report measures; and 3) one-month follow-up (e.g., social anxiety). Participants in the self-compassionate writing condition had higher confidence, eye contact, and state self-compassion compared to those in the control writing, but not the no writing condition. Exploratory analyses found that greater levels of fear of the upcoming task attenuated the effect of self-compassionate writing. Overall, results suggest that self-compassionate writing about a future anxiously anticipated event may be beneficial and that a fruitful direction for future research is to elucidate the utility of self-compassion for coping with anticipated difficulties.