Parents experience lasting psychological distress after a child’s death from cancer. Limited evidence exists regarding difficult life events, duration of psychosocial impacts, and associated risk factors among bereaved parents. Alex’s Lemonade Stand Foundation surveyed self-selected, bereaved parents regarding difficult life events and psychosocial wellbeing (life satisfaction, unanswered questions, and missing the care team) through a public, cross-sectional survey. 176 bereaved parents (89% mothers) participated a median of 7 y after their child’s death. The most difficult events were family vacations (80%), their child’s birthday (80%), and anniversary of their child’s death (76%). Only the latter did not improve with time. Greater life satisfaction was associated with male sex (ARR = 1.2, 95% CI:1.1–1.4) and being married/partnered (ARR = 1.2, 95% CI = 1.0–1.3). Having unanswered questions and missing the child’s team were associated with annual income <$50,000 (ARR = 1.2, 95% CI:1.1–1.2; ARR = 1.2, 95% CI:1.0–1.3, respectively). Pediatric oncology programs need robust bereavement programs that include prolonged contact with families.