Insecure shook fans to their core. Despite the fact that viewers are used to taking sides over the men in Issa's (Issa Rae) life — Lawrence (Jay Ellis) vs.
whoever the fine ass flavor of the month is — Season 4 delved into a breakup significantly more earth shattering than a romantic one.
As Issa and Molly (Yvonne Orji) were finally reaping the professional and personal benefits of their hard work, they found they had grown so much that they didn't quite fit together anymore. "All the relationships in the show, are they for a reason, a season, or a lifetime?," said Prentice Penny, showrunner of Insecure, in a phone call with TV Guide.