Insecure's Issa Rae Has One Major Regret About Issa Dee's Storyline

When Issa Rae's "Insecure" premiered on HBO in 2016, her character, Issa Dee, was a 20-something Angeleno with an unfulfilling non-profit job and an uninspired couch potato boyfriend. Over the course of its five-season run, "Insecure" demonstrated the realistic arc of coming into adulthood, not only through Issa's journey but also via its side players Molly (Yvonne Orji), Kelli (Natasha Rothwell), Tiffany (Amanda Seales), and Lawrence (Jay Ellis).

For 2021's series finale, "Insecure" careened forward into the future to follow the gang well into their 30s, focusing on major life events like birthdays, pregnancy announcements, and weddings. "I went on my own journey as I filmed the season and lived as Issa Dee," Rae told Vulture, calling the final episode an "ending that paid tribute to the season as a whole."

However, Rae doesn't look at her show without regrets. "From the pilot, Issa lives in the what-if," Rae continued, meaning there were infinite ways that the series could unravel — and plenty of storylines she wishes she could have delved into. "I do wish we could've explored motherhood through Issa," Rae said, explaining, "since it is so present in my life right now, and I'm curious about it."

Babies and motherhood do make their way into "Insecure," but it's via the show's ancillary characters. Lawrence and his ex, Condola (Christina Elmore), have a baby together, and the series explores child rearing while separated. The show also looks at Tiffany's struggle with postpartum depression. Still, Rae indicated it would have been illuminating to show Issa going through that process.

While pregnancy and motherhood are narratively interesting to Rae, the decision of whether or not to have children is just as compelling. "That is something super real that we discussed in the [writers] room," Rae said in the same Vulture interview. "Women having this ticking time clock that's so unfair that men will never experience ... There was an interesting discussion that happened in the room that men were enlightened by — annoyingly so — that the women in the room really bonded over," she continued. "Even if you don't want kids, you still feel that clock."

Rae and the "Insecure" writers briefly addressed the weight of that choice in the finale, when Kelli, who had previously said she didn't want children, announces she is pregnant. But in an already jam-packed finale, the moment doesn't get the depth of conversation it deserves. "That's something I wish we were able to explore," Rae said about "Insecure" before alluding to future projects. "Maybe we'll explore it with something else."