Editor’s Note: The following contains spoilers for Hacks Season 4, Episode 6

Ever since that brutal, stomach-churningSeason 3 finale twist onHacks, whenHannah Einbinder’s Ava blackmailedJean Smart’s Deborah into giving her the head writer position onLate Night, it’s been clear that the mentor-mentee bond we’ve watched evolve over the years was permanently damaged.Ava did something so devastating, so sinister that one can’t help but wonder if the pair would ever be able to come back from it. She did this, of course, because all of Deborah’s personal and professional transgressions had finally reached a boiling point. Deborah didn’t break Ava’s heart just because she lied to her about the job; she broke her heart because she was willing to toss out all of their shared history and lose her as a friend as well.

Hannah Einbinder’s Ava staring at Christina Hendricks' mysterious character in Hacks Season 3

Season 4 ofHackshas masterfully continued this storyline and explored all the complicated nuances that go into a relationship so heavily reliant on trust. Unsurprisingly,Deborah’s gotten back at Ava in very petty ways, such as when she hilariously planted Ava’s underwear in their boss Rob’s (Dan Bucatinsky) office, hired her eccentric psychic Diana — played perfectly byPolly Draper— as a consulting producer, and made Ava take a drug test due to an “anonymous source” making complaints about her. However, it’s when Deborah has Ava’s actress ex-girlfriend, Ruby (Lorenza Izzo), as a guest on her talk show in Episode 6 that we see Deborah make one of the most egregious decisions yet — and hit an entirely new low in the process.

Ava’s Love Life on ‘Hacks’ Is Consistently Messy

If there is one thing that Ava is good at, it’s having really, really complicated relationships.Hannah Einbinder’s performanceas the bold, outspoken, determined comedy writer perfectly brings to lifeAva’s lovable — and at times, deeply problematic — character flawsthat inevitably shape her turbulent love life. Einbinder makes us cringe, laugh, and cry, but above all, she makes us care deeply for Ava. This sentiment gets thrown around a lot when actors nail a performance, but it is truly impossible to imagine anyone else but Einbinder in this role.

Over the course ofHacks' four sharp seasons, Ava’s been involved in a number ofsexual situations that are as unpredictable as they are unfiltered. In Season 1, her Las Vegas hookup with George (Jeff Ward) ends in an unimaginable tragedy when, the day after their wild night of sex, drugs, and partying, Ava discovers that George jumped to his death.Season 2 gifted uswith that epic lesbian cruise episode, and in Season 3, Ava falls fast and hard for a mysterious woman at a golf tournament, only to awkwardly learn in a moment of passion that said woman — played with a hilarious deviance byChristina Hendricks— is only attracted to Ava because of the power dynamic, given that Ava is a lowly caddy. (She’s also a Republican, which just further mindfucks Ava in more ways than one.) Most recently, Ava becomes the third in a throuple with a married couple she meets while buying a dildo in a sex shop (long story). But the one throughline has been her on-again, off-again girlfriend, Ruby.

We’ve Never Seen This Side of Deborah on ‘Hacks’ Before

Ava and Ruby’s Relationship Has Always Been Complicated on ‘Hacks’

One of the first things we learn about Ava is howdeeply insecure she is in her relationship with Ruby. Part of Ava’s charm is her knee-jerk instinct to lean into self-deprecation, but when it comes to Ruby, it’s clear she genuinely feels inadequate and that she needs to follow up every “This is my girlfriend” with an “I know…crazy, right?” One of the first traumatic moments Ava has with Deborah is when she is caught taking nudes in Deborah’s office for Ruby.

Ruby always felt like she was taking the back seat to Deborah, and anytime she called Ava out about her unhealthy relationship with Deborah, screaming typically ensued. Ava is blinded by her love for Deborah, and in Season 3, Ruby hits her breaking point. Ruby and Ava make the difficult decision to pull the plug on their romance, even though they have something special.

Lorenza Izzo’s Ruby as a guest on Late Night with Jean Smart’s Deborah Vance in Hacks Season 4, Episode 6

SinceDeborah and Ava’s relationshiphas somehow survivedall that it has, these two understand each other on such a deep level that they know exactly how to twist the knife in a way that will emotionally eviscerate the other. Season 4 has explored this notion thoroughly. Each insult is more specific, more pointed, and thus, more personal.

Deborah and Ava Feel Immense Pressure To Deliver a Strong Show in ‘Hacks’ Episode 6

By Episode 6 of Season 4, Deborah’s ego is deflated and is desperately trying to return to its typical, enormous form. She finds out she’s getting a comedy award, but it’s actually just a PR stunt to get some positive press forLate Night. She’s coming off a frustrating focus group which lowered her self-esteem. Plus,Chercancelled her appearance at the last minute because she… just didn’t want to do it. (Classic Cher.) Luckily, the lead from the popular showWolf Girl— who happens to be Ruby — is available.

We’ve Never Seen This Side of Deborah Before on ‘Hacks’

“It’s a cardiac issue!”

Ava is visibly uncomfortable with the last-minute booking idea,even admitting to everyone that she and Ruby almost got married. The entire episode is a struggle for Ava, who reverts to the insecurities she had about herself when they were dating. She frantically gets a makeover, and tries (and adorably fails) to be “cool” when talking to Ruby before the show. Understandably,Ava’s got some pre-show jitters, and is heartbroken watching Ruby laugh it up with Deborah. Ruby certainly wasn’t perfect in their relationship, but Ava is undoubtedly second-guessing every decision she’s made, wondering what she could have done differently, and what could have been.

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Deborah Knew How Much Ruby’s Story Would Traumatize Ava

Deborah, furious with Ava for having sub-par material for that night’s show, decides to cut the bit Ava prepared and instead extends the interview with Ruby to fill the time. What should’ve remained a benign, surface-y interview takes an abrupt personal turn for Ava.Deborah takes a sudden interest in Ruby’s props on set, and cheekily asks her to tell the story she “heard” about an ex with a ring. Ruby is visibly uncomfortable and even makes eye contact with Ava off-stage in an “is this really happening?” sort of way. Feeling put on the spot by Deborah and trying to maintain her public image, Ruby attempts to tell the story about how Ava (the unnamed ex) found the prop ring fromWolf Girland thought Ruby was going to propose to her, in the most palatable and respectful way.

Ava’s eyes swell with tears of embarrassment, utterly shocked that Deborah wouldreally go there. Deborah’s working relationship with Ava had already ruined Ava’s relationship with Ruby, and Deborah knew that. To take it a step further and make Ava feel humiliated as she relives that embarrassing moment when she decided to propose to Ruby with the prop ring — only to be in the middle of a devastating misunderstanding — wasan entirely new level of petty and petulant behavior from someone abusing their power. Deborah takes the easy way out with the interview, and no one gains anything in this segment other than her. Even though Deborah and Ava have gone through hell and back, Deborah prying such a personal, painful anecdote from Ruby about her past with Ava felt needlessly vicious, and sinks Deborah to a whole new low.

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Hacksis available to stream on Max in the U.S. New episodes drop every Thursday.

Explores a dark mentorship that forms between Deborah Vance, a legendary Las Vegas comedian, and an entitled, outcast 25-year-old.