Favorite Characters: Issa Dee (Insecure)

 

I love rooting for a 20-to-30-something character who’s still trying to figure their life out. That might be an “easy” genre, kind of overplayed, but when it’s done well, it still hits home. In Issa, Insecure has a lead that’s messy, awkward, engaging, and likable in the midst of all her faults (a few Issa-related spoilers.)

Even though Molly, who’s much more type-A, is an easy character to peg as always having a plan, that kind of applies to Issa too. The only trouble is, a lot of her plans are New Year’s resolution-esque, big intentions that she struggles to follow through on. When we meet her, she’s just turning 29 and has started to realize that her goal of having all her shit together by the time she’s 30 has fallen off track. She’s not excited about her job, her relationship seems to be in a holding pattern, and she’s going along with things instead of going after what she wants. She makes a big declaration of changing all that, of becoming a “new” Issa and discarding all her old bad habits.

But the follow-through on that goes in fits and starts. She makes a big swing to speak up at work, but then, when she’s given the sort of opportunity she’s been wanting, she thinks she can wing the presentation. She decides she’s going to leave her stale longtime relationship and reconnect with her what-if guy, but rather than making a clean break with Lawrence, she just avoids the issue and winds up getting into a messy situation involving both guys. In her friend group, she’s known as the one who’s still kind of floundering, and no one is ever surprised when one of her resolutions falls through.

Despite appearances, though, Issa is (very slowly) making her way toward progress. After a few false starts, she really steps up at the non-profit where she works and brings good ideas to the table, taking the time and putting in the work to do things right. Her plan to leave Lawrence and get with Daniel doesn’t go the way she hoped it would, but it does shake her out of some complacency and make her evaluate what she really wants in a relationship. And when she finally hits upon an idea that she’s really passionate about, the Inglewood block party, she manages to scrape through the various disheartening setbacks and forge ahead, accepting help where she needs it to make her dream happen.

Of course, Issa still has a ton of things she has to work on. She’d almost always rather put off a problem than address it, she resents others for bad behavior she practices herself, and like a lot of protagonists, she can get wrapped up in her own problems and not realize how she’s monopolizing a relationship. But she remains smart and imaginative, dreaming up neat ideas even if she doesn’t know how to execute them, and over the seasons, she’s gotten better at brushing herself off and pressing on. I like different montages the show has done of Issa taking ownership by literally getting her house in order, like when she fully unpacks her new apartment at last after leaving boxes sitting around for who knows how long.

Side note: I really enjoy Issa’s sense of style. I live for her collection of message tees/graphic tees, I like that she’s often more dressed down than her friends, and I like seeing how she frequently changes things up with her hair. I don’t always pay a lot of attention to a character’s look, but Issa’s is done in such a way that really accentuates the feel of the character.

Relationship Spotlight: Issa Dee & Molly Carter (Insecure)

 

I already brought up these two quite a bit when I reviewed Insecure, but I wanted to give them their own post. Some female-led shows are “Queen Bee” types, where the female lead is surrounded mostly by guys and, if anything, is kind of combative with other women. In others, the female lead has a female best friend who’s largely a one-dimensional supportive sounding board, while in others, there will be a female character who’s referred to as the female lead’s best friend, but the two are rarely seen really acting like friends. In Issa and Molly, Insecure spotlights a female friendship that’s incredibly deep and complex, and I love it (some Molly-Issa-related spoilers.)

Right from the pilot, the show places Issa and Molly’s relationship front and center. For a series that’s often about romance drama and career struggles, both are frequently filtered through the conversations Issa and Molly have about them, decompressing over dinner or drinks, hashing things out on a car ride, calling one another at work to vent, or engaging in a late-night soul-bearing session at one or the other’s apartment. Whether they’re giving each other advice or encouragement, or maybe just a good, “Girl, what were you thinking?!”, each is the person the other most wants to talk to when something big goes down.

I appreciate, first of all, that even though Issa is definitely the lead on the show, Molly isn’t framed in a subservient role to her as a character. That might seem like an odd thing to even note, given that Molly’s an ambitious lawyer and Issa is kind of floundering in the non-profit world, but I mean it in more of a meta way. Molly doesn’t exist solely as a person for Issa to talk about her problems to, and Molly absolutely has a full life going on outside of her scenes with Issa. What’s more, they both come to each other with their problems, and they both listen to each other. There’s nothing one-sided in the dynamic of their relationship.

Which is interesting, because that goes for their relationship’s good and bad qualities. Just as they both are often there to support each other, both sometimes get self-centered and take the other for granted. They’ve both taken advantage of the other, both let the other down in a really important moment. When they start to have a hard time in season 4, both begin to drift from the other, not prioritizing their friendship like they used to. Both recognize a problem and their own part in it, but at the same time, they both feel like the other isn’t noticing it the way they are and feel hurt by that.

Even though all that goes down between them here is hard to watch, I kind of love it too. Because it’s such a strong depiction of a slow-motion friendship breakup, and in watching how the relationship starts to splinter, we see on both sides how Issa and Molly are affected by it, how much it meant to them in the first place.

In a weird, awesome way, I’m a little reminded of Marvin and Whizzer in Falsettos. Those two start out much more openly competitive/combative with each other than Molly and Issa are, but the similarity lies in the way both pairs play emotional chicken with one another in a clinch moment. With Marvin and Whizzer, it’s about admitting that they love one another, and with Molly and Issa, it’s about being the first one to make an overture to acknowledge where their friendship has started to come undone and do something to try and fix it. Each feels let down by the other, thinking that they’re the one who’s always the first to apologize, always the one doing the work. So each digs in their heels and thinks, “Not this time. This time, she has to go first.” And all the while, they’re both being eaten up by missing each other, holding on to their perceived moral upper hand and being miserable about it. It’s a reckoning that’s a long time coming, and the show resists an easy answer to instantly knit everything back together.

In short, it’s the kind of engrossing plotline that you normally see devoted to a romantic relationship, and I so appreciate that we see it here in the context of a friendship.