Miserable. Hater. Controlling. Judgmental. Chances are, if you’ve been tuned into the fourth season of HBO’s Insecure, you’ve called Issa’s best friend Molly (Yvonne Orji) all of the above and everything in between.

Since its premiere, Molly has been scrutinized for being the friend everyone hates. You know the type: the critical know-it-all, the uppity one who refuses to let loose and just enjoy life.

But as an attorney myself, with plenty of friends in the profession, it’s obvious that a lot of who Molly is, and how she shows up in her relationships, is informed by her identity as a lawyer. Both in school and in practice, attorneys develop sharp critical thinking skills that enable us to identify potential risks to our clients. Although Molly’s behavior may not be the most becoming at times, it’s certainly consistent with the qualities we love to hate about lawyers. Trained to be cautious, pragmatic and assertive, in each conflict presented to Molly, she does what she was taught: gather the facts, assess the risk and proceed accordingly.

And although most lawyers don’t allow the profession to define who we are as people, almost all of Molly’s behavior can be chalked up to the blurred lines between who she is as an attorney and who she really is as a person. Let’s take a deeper look at four times Molly “lawyered” her way through life:

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As Molly and Andrew’s relationship steamed up this season, Molly noticed Andrew (Alexander Hodge) avoided vulnerability about his struggles at work and with his family. Knowing she wanted their situationship to evolve beyond Porto’s and sex, Molly rightfully questioned whether Andrew could engage in deeper conversation. Even when everyone, including Andrew, criticized her for making “everything an issue,” Molly was simply being vocal about what she needed from Andrew, and cautious of entering another relationship that didn’t meet her needs. And isn’t that what we tell ourselves to do; reflect on our needs and not allow people to invalidate our feelings? Molly made the right decision.

Lawyers have a tendency of operating solely based on facts and negating emotion. So when Issa (Issa Rae) called Molly to ask for help after Schoolboy Q backed out of her inaugural Block Party a few episodes ago, it was almost a reflex for Molly to ask Issa if she had a contract. As insensitive as it may have seemed, Molly’s brief interrogation about why the contract was breached was her attempt to resolve the issue in black and white, with no room for grey. Exacerbated by her disappointment that Issa wasn’t calling her for girl chat, she resorted to lawyer mode. By compartmentalizing the legal issue presented by Schoolboy Q’s cancellation and dismissing Issa’s need for support, Molly did what lawyers do best: search for logic and ignore feelings. Thankfully for Issa, the line-up for her Block Party worked out with Vince Staples taking the stage.

After Molly learned that Issa’s ex, Lawrence (Jay Ellis), was now dating Issa’s new Block Party-planning bestie, Condola (Christina Elmore), her antennas went up. It didn’t help when Molly saw Lawrence and Issa kiki-ing in Tiffany’s (Amanda Seales) courtyard. It was obvious Molly pictured the love triangle blowing up in Issa’s face and her being forced to pick up the pieces; a role she is obviously tired of playing. Call her pessimistic (I personally prefer the term, risk-adverse) but lawyers are trained to foreshadow the future and consider that everything that can go wrong, eventually will. Since we’ve all seen how the triangle played out, it’s safe to say Molly wasn’t wrong for being concerned. Lawyers be knowing.

During last Sunday’s episode, was Molly wrong for going off on Issa at her Block Party, the culmination of months of planning and a hard-won achievement for the former “struggle friend?” Yes. But was Molly wrong for asserting the boundaries she set with Issa? No. Although the time and place was completely inappropriate, one thing lawyers are never afraid of is voicing their opinions. While Molly didn’t exercise the best judgment timing-wise, the strongest lawyers assert themselves, especially when they are clear about their intentions and someone circumvents them. In that moment Molly was out of line, but so was Issa. Let’s just hope their friendship can survive it.


Whether you agree with the way Molly approaches life or not, you have to admit, she’s merely conformed to the mindset lawyers are often celebrated for. Are we over-analytical and sometimes annoying? Maybe. But I bet they’re also the first friend you’d call if your landlord was tripping or you were starting a business and needed some direction. So the next time you draft that tweet ready to drag Molly, show her a little grace. Is she the most compassionate friend? Maybe not. But does she care about her friends making good choices that will ultimately benefit them? Absolutely.

Case closed.


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