The Rise (and Fall) of the Sad Girl Grifter

A grifter is, plainly, someone who lies, cheats, steals, or manipulates their way to a desired end. This archetype has been around as long as storytelling itself, but it’s actually made up of several highly differentiated sub-archetypes.

For example, the jolly grifter (Robin Hood) is altogether different from the angry grifter (Patrick Bateman from “American Psycho”); the cold grifter (Tom Ripley from “The Talented Mr. Ripley”) is easily distinguishable from the greedy grifter (Bernie Madoff).

Grifters can be analyzed by affect (jolly, cold, angry, greedy, sad) and/or by gender. How does Pippi Longstocking differ from Robin Hood in what she is allowed to do? How is Sam Bankman-Fried treated differently from Elizabeth Holmes?

The SGG, like the grifter in general, is willing to do the unsavory to achieve her goals.

In my writing, I find myself particularly drawn to the Sad Girl Grifter (SGG). I’m intrigued by her for many reasons, but primary among them is the fact that she is doomed to fail by the very structural forces that led her to rise in the first place.

The SGG, like the grifter in general, is willing to do the unsavory to achieve her goals. But her motivation, actions, and payoff are fundamentally different from those of her archetypical brothers and sisters.

In terms of motivation, the SGG operates from a place of resignation or rock bottom. The cold grifter, on the other hand, is usually motivated by sociopathy or emotional detachment. The greedy grifter? By ambition. The jolly grifter? By the sheer fun of the game.

The SGG is operating against a system that she believes has abandoned or failed her in some way. Her “grift” is then used to exploit or expose said system. She’s not just a criminal, but a critic. She uses emotional appeal as leverage to succeed in her grift, and employs narrative self-justification to explain her grift to herself and others. She may believe in her own lies as a matter of survival.

The SGG isn’t punished for lying or cheating or stealing, but for wanting too much, for going beyond what is societally expected or acceptable.

And what’s the payoff for all of this? This is where the grifter archetypes tend to differ most. The jolly grifter gets away with it. The angry and cold grifters usually do, too. The greedy grifter lives on in infamy. The sad grifter? If he’s male, he may get away with his grift. The SGG doesn’t have as much luck.

An important note is that failure does not necessarily equate to jail time or death or complete self-destruction. To fail in one’s mission can be more subtle. Think about it this way: Does the grifter get to keep what they took?

And the real differentiation doesn’t always come from whether the grifter fails or succeeds in their mission; the nature of the grifter’s success or failure can be just as indicative. The SGG isn’t punished for lying or cheating or stealing, but for wanting too much, for going beyond what is societally expected or acceptable.

While the general grifter is allowed to reinvent themselves, be openly ambitious, and romanticize their crimes, the female grifter—and especially the SGG—is met with significantly less permission and a higher demand for likability.

Of course, there are male grifters who fail. But this failure is often heroicized: when our male grifter fails, he fails beautifully, and his downfall confirms his complexity rather than condemning his actions. It’s often the case that even when the male grifter loses, the narrative insists that he was right to try.

Consider Don Draper from “Mad Men.” He is a classic sad boy grifter. He steals a dead man’s identity, cheats on his wife, and manipulates people into buying things they don’t need. His life is one big con. But we accept him and grant him tragic grace. We treat his grifting as evidence of emotional depth.

The SGG doesn’t get the same treatment.

The SGG is rarely capable of success in her grift—not because she lacks the proper skills or intelligence, but because the system she exploits as part of her mission does not allow her to win.

In my novel “Just Watch Me,” the protagonist, Dell Danvers’ little sister Daisy is in a coma and she is outraged by the astronomical medical cost of keeping Daisy on life support. At the same time, Dell notices the popularity of platforms that let people raise money, and the rise of the creator economy, where a person can be rewarded for putting their rawest self on display.

The SGG doesn’t fail because she’s bad at her con, but because her success would require a culture that is willing to let women want openly, take what they want, and keep what they take.

She decides to take advantage of these systems, starting a livestream and doing increasingly dangerous dares to raise money for Daisy. She knows these systems are flawed, and she sees a narrow space for herself to exploit those flaws.

She doesn’t “fail” because she lacks the skill or ability—in fact, she proves to be a very talented streamer—but because she wants too much. Dell saw a flawed system (the attention economy), and sought to exploit it in order to overcome another flawed system (medical bills), which is what makes her “sad” in a deeper sense: she saw the game clearly, understood the limits of the system, and decided to play anyway.

Just because the SGG has not historically succeeded, that doesn’t mean she can’t continue to try. In fact, we may be entering a perfect cultural moment that makes the SGG a particularly compelling subject.

We’re seeing the rapid growth of the creator economy, where emotional intelligence is rewarded. In a content culture where authenticity is queen, the SGG’s nature and manipulation skill let her play-act authenticity with the best of them.

Writers with an SGG in mind may write towards these perspectives in first person or a close third, using a confessionary voice. Their protagonists may be intelligent and quietly manipulative, their aims rife with social or cultural commentary. And perhaps the most telling aspect of an SGG narrative is audience complicity, garnered through narrative intimacy.

While the greedy grifter operates through speed and scale, and the angry grifter operates through ideology, the SGG’s modus operandi is closeness and narrative control to win you, the reader, over.

There are risks of writing from the SGG perspective, just like there are risks of writing from the perspective of any deeply-flawed protagonist. The biggest risk of all lies in the fine line between empathy and endorsement. We can’t confuse a beautifully crafted narrative with faultlessness (think: Humbert Humbert in “Lolita,” who is a classic sad boy grifter). We can understand someone without absolving them.

The SGG doesn’t fail because she’s bad at her con, but because her success would require a culture that is willing to let women want openly, take what they want, and keep what they take. For now, the SGG is allowed to rise only until her level of ambition or desire becomes societally untenable—then her audience demands punishment.

But each failed attempt widens the crack just a bit. And until she’s allowed to succeed, the SGG will continue to do what she does best: expose the system by failing inside of it.

__________________________________

Just Watch Me by Lior Torenberg is available from Avid Reader Press.