Issa Dee considers her choices in a fantasy-driven Insecure

A few weeks ago, we watched Issa debate her life choices in the hilarious “Tired, Okay?!” That episode made it clear that Issa still has feelings for Lawrence and she isn’t exactly sure about Nathan. “Choices, Okay?!” revisits the same debate, but shows that Issa’s uncertainty has spread to her career decisions. Issa feels like she’s at a crossroads and Eli Wilson Pelton’s script uses Mirror Issa and some Sliding Doors-like magic to envision the various paths ahead of Issa.

The thing is, it doesn’t really feel like Issa has to make an all-or-nothing choice when it comes to NBW and Crenshawn. The three have all partnered together in the past, so there’s no obvious reason why Issa seems to think these two opportunities are at odds with each other. Pelton’s script acknowledges this: as Molly says, nothing is ever black or white. Issa will be okay, no matter what she chooses. The scenarios she imagines are driven by her own fear of missing out on what could’ve been.

For Issa, the grass will always have more Ty Dolla Sign on the other side. “Choices, Okay?!” isn’t really about Issa’s career insecurities since each scenario only reveals that she’s beginning to doubt her feelings for Nathan more and more. Eventually, she even starts to hear Lawrence when she’s with Nathan. Perhaps, Issa isn’t really backtracking and it was Nathan’s suggestion that they move in together that triggered Issa’s flight instincts. It’s possible she does love Nathan, but she’s not ready to move in with him. Everything is moving forward in Issa’s life and Nathan is still connected to the Old Issa who has to deal with annoying tenants. Issa makes it clear that she wants to be a power couple and Lawrence is now more aligned with that vision.

And honestly? Nathan doesn’t even look right in Issa’s fantasies! Issa can’t even imagine Nathan doing anything beyond what he’s doing right now with his men’s group. She doesn’t really see a future for them as a couple and she’s finally admitting that to herself. Does that mean she’ll finally end things with him? Sadly, I don’t think she will. It’s like Issa almost has a moment of clarity, but she’s afraid to admit that Lawrence is still the person she truly wants.

Molly acts as our anchor to reality in “Choices, Okay?!” She’s dealing with her parents’ will and her feelings for Taurean. Rather than lash out at him or cancel their date without revealing anything personal, she actually shares something intimate with Taurean! Which allows Taurean to be there for Molly in the way she needs! Now that’s growth! Look at Molly go! Ordering delivery for someone is an incredibly sexy move and Molly deserves someone who understands when she needs space.

Last week, I said Kelli’s unhappiness with her career felt a bit rushed. We haven’t heard much about what Kelli does, so this sudden desire to change paths is a little random. Pelton’s script connects the dots between this and Molly’s story as Kelli steps in to help her parents organize their finances. Kelli does have a natural way of getting them to open up, but something about these moments feels more PSA-like than inspirational. It’s not until Molly breaks down in her car that the real weight of providing for parents who can’t take care of themselves is understood. Molly puts on a happy face for her parents, but at least she’s telling someone how she really feels.

With two episodes left, it feels a bit late for Issa to still be this conflicted over the choices she needs to make. At this point, if she wants Lawrence, I just want her to go for Lawrence! Let’s stop playing these flaky games with Nathan when the two don’t have much of a spark anyway. Nathan has always felt like a rebound and “Choices, Okay?! suggests Issa finally sees that for herself. I’m ready to see Issa make some firm choices when it comes to her love life.

Stray Observations

• The men not knowing how to pose for the picture was perfect.
• Issa’s event went well and we got to see her brother again! He still hates Kelli, their feud is great.
• I wish we could’ve seen Molly and Taurean’s first date!
• That apology from Crenshawn was pretty sexy. I still think this is the relationship Issa needs to focus on!
• We haven’t seen Issa have a mirror moment in awhile, but it makes sense that Mirror Issa would return in such a fantasy-based episode.
• Issa makes up for no one rapping with her during the panel in this season’s premiere by dreaming up a scenario where everyone sings with her!
• Not Tyra Banks giving Issa the key to Inglewood!
• Not sure where Tiffany was this episode. You’d think she’d be spending as much time with the girls as possible since she’s moving.
• Do you think Lawrence is ever like “Issa left me because I wasn’t successful enough and now she’s dating a barber with roommates?”