Who would have thought that after all of the failed relationships and situationships on HBO’s Insecure, I would still get so giddy at the possibility of new love for one of its main characters? I’m pretty jaded about finding love in real life, so why did I squeal with delight multiple times during “Fresh-Like” watching Issa (Issa Rae) having a new boo? Perhaps it’s because I think that Issa, of all of Insecure’s characters, deserves happiness. It looks like she might be well on her way. Read on to find out who the new guy is that Issa will inevitably have to stalk on the internet.
The first and most important thing that you need to know is that the mirror freestyles are back! “Fresh-Like” opens with Issa flowing about her new living space and addressing herself in the third person as “mirror bitch.” And when Daniel (Y’Lan Noel) unexpectedly knocks on the door to drop off the last of Issa’s things, “mirror bitch” actually speaks back after Issa walks away. Clearly the creators at Insecure want in on the surrealist movement happening in Black Hollywood, and I love it.
Anyway, I love that Daniel appears in this capacity — in service of Issa but clearly a little salty about it — because it comes with a message that more women need to absorb. No matter how annoying or inconsistent the men on Insecure may be — from Daniel to Lawrence (Jay Ellis) — they still operate on foundational principles of respect and courtesy. And the writers on Insecure remind us each week that polite men can still be trash, or at the very least, not for us. They aren’t owed praise or sex for being decent humans. Daniel doesn’t get a cookie or any brownie points for helping Issa move. And the curt greeting that Molly (Yvonne Orji) gives him on his way out (and the fact that we don’t see him again in the entire episode) is a visual representation of the indifference that women are allowed to have about men like him.
The two best friends spend the day helping Issa unpack. In the process, Molly finds a bunch of junk that Issa needs to throw away: a book by urban erotica writer Zane (an embarrassing reminder of my own middle school interests), a box of Forever 21 earrings (I don’t understand what the problem is here), and some mix CDs that Lawrence made for Issa after their first date (girl, burn them). Molly is insistent that if Issa is to truly have a fresh start, she needs to stop lugging around these mementos from the past. At first Issa goes along with the purge, but later that night when Molly is gone, she removes all of the aforementioned items from the trash. But I wouldn’t worry about Issa just yet. It could just be that she needs a little bit more time to decipher what is worth keeping and what parts of her past can be useful moving into the forward. Hint: the high school rap journal she found should probably stay.
Per usual, Molly has great advice for Issa but is struggling to navigate the difficult situations in her own life. It’s one of the things that the lawyer and I have in common. One of her male colleagues — a pompous Morehouse graduate — talks over her in a meeting before she can share her own ideas, and it bruises her ego. However, his mansplaining creates a bridge for her to relate to a couple of the Black female lawyers at the firm; solidarity that she desperately needs right now. The question is, though, does Molly know that she needs this camaraderie? That is yet to be revealed.
Molly does know that she still needs therapy. I’m grateful for her self-awareness, even if I do feel sorry for her therapist. Dr. Rhonda Pine (Denise Dowse) is probably so tired of listening to Molly be self-absorbed, but that’s why she’s paid the big bucks. Anyway, after Molly vents and talks over Dr. Pine about why she isn’t being celebrated more at work, Dr. Pine asks: “Have you considered that maybe you’d be less frustrated if you focused on how you can be helpful, whether than where you rank?” A friend called me self-absorbed last week, so I feel like there was a message in there for me. I’m going to receive it, unlike Molly, who is hell bent on not accepting anything less than perfection. She sees this as the mistake she made with Dro (Sarunas Jackson), her married former lover that Dr. Pine knew nothing about.
At We Got Ya’ll, Issa looks out at the sea of white faces at the organization that is supposed to empower students of color, and she is over it. It’s written all over her face. But her day is about to change for the better. For one, her co-worker Frieda (Lisa Joyce) has some good news: their boss Joanne (Katherine Kurtain) has agreed to let Issa return to the field and work directly with the students they serve. That doesn’t change the problematic racial dynamics of the organization, but at least it takes her off of desk duty. Then she runs into Nathan (Kendrick Sampson), the $50 tipper from her season premiere “party Lyft,” at a taco joint.
Warning: My squealing commences now. First of all, the chemistry between Issa and Nathan is so natural and cute. He refuses to apologize for his disdain for L.A. (same, bro), and she refuses to stop defending her beloved city. In fact, they spend the day on an Issa-led tour of some of the city’s Black neighborhoods, including the one where Issa grew up. Issa has way more “game” than I gave her credit for, keeping an arsenal of flirty one-liners at the ready for Nathan, who is adventurous and unfiltered. *squeals* His energy is apparently infectious because as their run-in becomes a full-on date, Issa calls in sick to work, breaks into her childhood home, skinny dips in the pool, and then runs when the owners threaten to call the police. In between the fun the pair is having together, Issa also feels vulnerable about the fact that she is passionate about rapping and that she cheated on her ex. *squeals* I’ve never seen our girl like this, and I’m honestly shook!
Bonus detail from Issa and Nathan’s date: They come across a bus bench ad for Chad Kerr’s (Neil Brown Jr.) realty business. In case you forgot, Chad was Lawrence’s BFF, and even though he was a sarcastic asshole, he was funny, and I miss him on the show. I don’t know if this is a sign that he’s returning to the series, but I hope so.
Every time I’m ready to root for Molly, she takes a step backwards. She seems to be taking Dr. Pine’s advice about being more helpful at work to heart when she volunteers to help her female colleagues on a case. However, when they try to schedule time to meet about it, she can't because she’s also made some sort of other arrangements with the asshole from Morehouse who spoke over her. Ugh.
At least there’s still hope for Issa. Her date with Nathan — which ended with a kiss — has completely changed her mindset. She decides to throw away those CDs and that damned Zane book. The rap journal stays. But that’s just the tip of her fresh-start iceberg. The next day at work, Issa does what she should have done in the very first season. She quits her job at We Got Ya’ll. Yaaaassssss! I can’t wait to catch the rest of what is sure to be a glow-up.
What I would have done if I was Molly: The difference between Molly and I is that I have a much stronger inclination to trust other Black women. It would be hard for the Morehouse man to even get a hello from me, let alone some of my free work time. She needs to stick to the code: breasties before testes. Also, I would leave a really big tip for Dr. Pine.
What I would have done if I was Issa: I love that Issa feesl so comfortable with Nathan, but I would have never ended a first date in my furniture-less apartment. Other than that, I’m glad sis is living a little, and I hope she makes at least one reckless purchase to celebrate quitting her job.