When it comes to toxic relationships in comic books, no love is more tainted than that of Harley Quinn and the Joker. The Bonnie and Clyde of Gotham, the Clown Prince and his former queen once matched wits against Batman as a romantic partnership—albeit an extremely one-sided and violent partnership. From her creation in Batman: the Animated Series in 1992 to her upcoming film Birds of Prey: And the Fantabulous Emancipation of One Harley Quinn set to release in February 2020, former Arkham Asylum psychiatrist Dr. Harleen Quinzel has always been depicted as a gullible genius who narrowly survives the consequences of loving the wrong person.

Though he may be one of the most fascinating villains in all of pop culture, the Joker is a terrible life partner. Arguably, the only person the Joker comes closest to actually loving is Batman, and he expresses that love by threatening Gotham. In regards to Harley, she is nothing more than a living extension of his own chaotic will. But despite originally being created as a meager one-episode henchwoman, designed to make the Agent of Chaos’s gang less of a sausage party, Harley has since evolved into a symbol of empowerment for many geeks who have also suffered at the hands of a charismatic abuser.

While she has been known to reunite with her Puddin’ in moments of weakness, for the most part Harley Quinn has forged a unique path as one of the most recognizable antiheroes in modern American fiction completely independent from the Joker. Below are 8 noteworthy moments in Bat-history where Harley Quinn was pushed a step too far and either turned against “Mistah J” (often threatening his life) or moved on from their relationship (often temporarily).

Harley Quinn #1 (2000)

Gotham’s homicidal eco-warrior Poison Ivy may dislike the vast majority of mankind, but Harley is one meat-bag that the guardian of the Green genuinely loves. When Harley springs the Clown Prince from Arkham, Ivy pays her a visit to deliver some harsh truths about her relationship with the Joker.

Initially in denial about the abuse she was suffering, Harley is eventually forced to admit she was wrong about the Joker after he shoots Poison Ivy (who was disguised as Harley). Seeing her friend take a bullet on her behalf woke Harley up to the toxic reality she was living in, that her “mad love” for the Joker would eventually lead to her death. Though this was a monumental leap for her character, she unfortunately returns to the Joker on several occasions during this point in her history.

Gotham City Sirens #19

For a time, Harley had a fairly good life co-habitating with her villainous besties Poison Ivy and Catwoman. Having Pamela and Selina around helped Harley grow as a person and made her temporarily forget about her psychotic ex. But a heated conversation with Catwoman in Gotham City Sirens #19 triggers years of trauma at the hands of the Joker and Harley goes on a manic quest to kill him out of revenge.

During her assault on the Joker, Harley reveals a nightmarish talent in using her intimate knowledge of the Arkham staff against them. Her obsessive need to murder the Joker was so severe she even willingly killed one of her former work friends just to get closer to her old Puddin’. Her rampage lasts an entire issue, all the while flashbacks of the pain she suffered throughout their relationship echo in her head. But when it came to finally pulling the trigger, Harley tragically went right back to falling under Mistah J’s spell.

Harley Quinn (the animated series)

The general theme of the DC Universe’s latest original show Harley Quinn is learning to leave an abusive partner. Despite it’s dark and clever (and very R-rated) wit, the show works in very deep metaphors. In the pilot episode, Harley is repeatedly abandoned and manipulated by the Joker, eventually forcing her former patient, Poison Ivy, to intervene.

By the end of the first episode, Harley comes to realize that the Joker doesn’t really love her—he only loves Batman. With the help of Ivy and the Riddler, the former Arkham doctor finally breaks the psychological spell she was put under. Harley ends the episode by wrecking the Joker’s hideout and brutally beating the hell out of his henchmen.

Batman: White Knight

In Sean Murphy’s non-canonical Batman universe, Harley leaves the Joker when she comes to realize that his obsession with his arch nemesis would always take first priority in his life. Furthermore, Mistah J’s “games” with his beloved Caped Cruasder were escalating to truly dangerous levels, eventually reaching a boiling point with the kidnapping of Robin, AKA Jason Todd. Though this version of Harley doesn’t have Poison Ivy pushing her to break up with the Joker, she leaves him all the same.

Harley briefly reunites with the Joker (who was going by his real name, Jack Napier) after she successfully orchestrates a scheme to make the Clown Prince go sane. As Napier, the Joker impregnated Quinn with twins before eventually losing his grip on reality again. In Murphy’s Curse of the White Knight, Harley appears to flirt with the Dark Knight, who helped deliver her twins.

Batman: the Animated Series “Harlequinade”

When the Joker steals a bomb powerful enough to turn Gotham into a smoldering crater, Batman enlists the help of Harley Quinn to track him down before the madman can hit the boom-button. Throughout the episode, Batman asks what she sees in the killer clown, and she responds by telling the Dark Knight that before she met the Joker her life was a boring routine of listening to other people’s problems—but with the Joker her life is full of laughter. Harley quickly proves her worth by tracking Mistah J to the mayor’s mansion just as Joker is getting ready to set the timer.

She betrays Batman at the first opportunity, but eventually turns on her Puddin’ when Batman and Robin point out that the Joker won’t just be blowing up the city, he’ll be murdering all her friends and even her pet hyenas. “Not the babies!” Harley then frees Batman, brings down the Joker’s plane with a ballistic jester scepter, and even tries killing the Clown Prince at the end of the episode (fortunately for Mistah J she accidentally grabbed the gag-rifle).

Batman: Assault On Arkham

In the animated film Batman: Assault On Arkham, Harley and Mistah J have seemingly broken up. During the film’s first act, Deadshot asks if Harley is going to be okay working a mission in close proximity to the Joker. She aggressively responds with “I’m fine. We’re done. He’s a jerk. Whatever.” Later on in the film, Harley enters Deadshot’s hotel room stark naked and looking to “scratch an itch.” Yahtzee!

After infiltrating Arkham Asylum, Harley further proves her hatred for the Joker by swearing and shooting at him in his cell (though this actually leads to his eventual escape). While these actions suggest that Harley really is going out of her way to move on from her relationship with the Joker, she eventually reunites with her Puddin’ by the third act of the story.

Birds of Prey: And the Fantabulous Emancipation of One Harley Quinn

While the film isn’t set to be released until early next year, both the trailers and cast interviews make it clear that the Joker (formerly played by Jared Leto) and Harley (played by producer Margot Robbie) are broken up. While their relationship in 2016’s Suicide Squad wasn’t as toxic as it has been previously depicted in other forms of media (electro-therapy aside), it eventually self-destructs all the same.

Although it is still unclear what exactly leads to their falling out, the fact that Harley is able to rebound and go on an R-rated romp with some gal pals suggests she’s happier without the clown dragging her down. If the trailers are any indicator, Harley doesn’t seem to miss Mistah J all that much. And for that, this film at the very least deserves an honorable mention in the “Harley leaves Joker” category.

Harley Quinn #25 (2016)

While the Joker may be an addiction that Harley has a hard time kicking, in Amanda Conner and Jimmy Palmiotti’s Harley Quinn series she manages to build a new life for herself far away from her toxic ex. Moving to Coney Island was one of the sanest decisions Harley has ever made, but when her boyfriend Mason gets sent to Arkham Asylum, Harley is forced to revisit her old life and finally get closure with the Joker once and for all.

In Harley Quinn #25, the pale-skinned manic murder pixie starts a riot in Arkham and breaks Mason out of his cell in the ensuing chaos. Unfortunately, Mason’s cell mate is none other than the Clown Prince. After revealing to Mason all the horrible things Harley did when they were still together, Harley decides to enter the Joker’s cell and “talk.” The talking quickly turns to fighting, and in a fit of rage, she pummels the Joker to near death. She ultimately lets him live, claiming death is exactly what he wants. Finally closing a very dark chapter of her life, Harley confidently moves on from her old boyfriend… and hasn’t gone back to him since.

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Toxic relationships are no laughing matter, but that is honestly what makes Harley Quinn so relatable and beloved by fans. Much like many survivors of abusive partners, Dr. Harleen Quinzel would not be the woman she is today without her awful relationship with the Joker. Their explosive relationship is meant to serve as a warning sign for people infatuated with monsters, but it also serves as a beacon of hope for people who find themselves stuck with toxic partners. Harley has made many mistakes in her life, but even after drowning in poisoned waters she still managed to kick to the surface and be stronger for it.

More: Harley Quinn Asks The BIG Question About DC’s New Suicide Squad