Insecure: Halfway through the season, how far have Molly and Issa come?

Issa and Molly have both seen major changes in their relationships and careers. Let’s track their progress in their mission to “know better, do better.”

As I’ve stated in previous reviews, the motto for season 3 of Insecure, at least for our heroines Molly and Issa, has been “know better, do better.” We’ve seen Molly try to do better in her career and dating life, and we’ve seen Issa try to improve her whole life in the aftermath of her breakup. Since we’re officially halfway through the season, it seemed like a good time to check in on our two favorite L.A. ladies and grade their progress.

Issa

Episode 20 (season 3, episode 4), debut 9/2/18: Issa Rae. Photo: Merie W. Wallace/HBO

In season 3 episode 4, “Fresh-Like,” Issa got off to a fresh start in more ways than one. She moved into her new place, and, at the end of the episode, quit her job at We Got Y’all.

Overall, as this season has progressed, I’ve been impressed, and sometimes amused, with Issa and her willingness to try new things. While Issa’s decisions may still not always be terribly well-informed, they’re demonstrating her newfound ability to step out of her comfort zone and not rely on old things or people. She’s making the most of her job, finding new ways to generate income and exploring life beyond her five-year relationship with Lawrence and, Daniel. I do kind of wish the show hadn’t immediately thrown Issa with another potential love interest, Nathan, as I’d love to see Issa just spending time alone. However, I did appreciate Nathan’s appearance as the final objective voice Issa needed to hear telling her the only thing holding her back is her.

It remains to be seen how Issa does as a property manager. So far, she doesn’t appear to be taking it too seriously, but who can blame her? After all, claims of squirrels in the walls and false accusations of lock-changing won’t win you a lot of credibility with any property manager.  Issa may not be here for her tenants’ loopy complaints, but her new role could be a precursor to her becoming more of a leader in her career and her life as a whole.

While I do appreciate Issa’s boldness, there were also times she needed to dial it back this episode. Which brings me to the final scene of “Fresh-Like,” where Issa spontaneously quits her job. Again, it’s cool to see Issa not staying content with mediocre or just plain terrible situations, but couldn’t she have waited until she at least had another offer lined up?

I get it, We Got Y’all sucks. It is racist inside and out and no one but Issa seems to care. That fact has been established over the last three seasons. However, given Issa’s financial situation, she needs whatever income she has, and she just gave up the security of a full-time job plus benefits, seemingly with no backup plan. What’s worse, Issa didn’t even have the self-awareness to have an “OMG what did I just do?!” moment after walking out of the building. Strutting into the sunset doesn’t have the same effect when you’re walking out of a guaranteed (at least for now) job. Issa’s setting herself up to end up financially on her back again.

To review:

• More confidence = good
• Independence = very good
• Having bigger goals for your self = great
• Quitting a job and possibly burning a bridge when you don’t have a plan B = extremely bad

Maybe Issa can still get her Coachella deposit back.

Issa’s mid-season “Do Better” grade