Social media has reconfigured how we express ourselves and in particular, our emotions. Grief is an emotion that is experienced globally and yet misunderstood. Features that are unique to social media have afforded social media users the ability to have new spaces and larger communities for expressing deep, complex pain and finding support online. This interdisciplinary study, leveraging expertise from social work, computer science and linguistics, explores how grief and daily stressors are expressed, on a digital platform, among Black Harlem residents and students attending a large university in New York City. We pay close attention to posts with features that reflect African American English and social media specific language. We created the Integrating Emotional Stories Online (IESO) to collect expressions of grief and everyday stress. The platform allowed participants to anonymously post and self-label their emotions that we analyzed using qualitative and computational topic modeling methods to identify core themes. We identified four primary themes that include expressions of interpersonal grief, systemic grief, everyday stressors, and self-care and joy.