And, as Sesali Bowen brought up during a post-finale debrief, if one of these relationships tanks, will Issa or Molly demand an impossible loyalty pledge from their still booed-up friend? After all, it's not like Issa or Molly can avoid their new bae's roommate, no matter how much their broken-hearted BFF might want them to. Prentice and Rae didn’t discourage the fact this uncomfortable scenario could be ahead, repeatedly saying such a situation is “real life.” Real life drama, as we’ve seen over the last three seasons of Insecure, is precisely what this HBO comedy is going for. There’s no reason to doubt season 4 will be any different.