20 Times ‘Orange Is The New Black’ Broke Our Hearts

Orange Is The New Black burst onto screens in July of 2013. It was the third original Netflix series to debut, after House of Cards and Hemlock Grove, and it took the world by storm.

In season five, the humor feels amped up quite a bit, but that doesn’t mean the series is any less serious.

There are still plenty of heavy moments that tug at heartstrings. They even sometimes provide explanations for why certain characters behave as despicable as they do which makes you want to sympathize with them.

It’s emotionally divisive in a way that sometimes feels too real.

More: ‘Orange Is The New Black’ Stars Dish On Piper & Alex’s Surprise Season 5 Ending

For those who haven’t quite finished, or even started, binging the new episodes, though, we’ve got a list of the most heartbreaking moments of the show up until the end of last season. But, be warned, if you haven’t caught up on the show there are potential spoilers ahead.

Initially shared by Screenrant, the list, starting from the bottom is as follows:

20. At the end of season three when the ladies break out through the fence and take that “Bittersweet swim in freedom lake.” It was great seeing them live freely for a moment, even though we knew it was fleeting.

19. In the season two episode “Little Mustachioed S***” when Vee convinces Suzanne, “Crazy Eyes,” to viciously attack Poussey in the bathroom. Poussey absolutely did not deserve that.

18. The episode where CO Humphrey, a prison guard, sadistically forces Maritza to choose between eating flies or a tiny newborn mouse. The look on her face when she realizes the futility of the situation is devastating.

Scroll Down For More Heartbreaking Scenes From OITNB

17. Taystee Shuns Poussey

When Taystee shunned Poussey because Poussey refused Vee’s business proposal. Vee made Taystee feel like she owed her devout loyalty and it drove a wedge between the two girls.

16. Vee did a lot of emotional, mental, and physical damage during her time on the show, but one of the worst was when she brutally attacked Red and then made Suzanne believe it was her who perpetrated the attack.

15. Sophia being a transgender inmate was never really an issue, until her son and Mendoza’s son became friends on the outside but had some trouble that caused a rift between the two ladies on the inside. Mendoza then started spreading homophobic rumors around about Sophia which led to her being attacked in a hate crime. This is a difficult scene to watch, but the real heartbreak comes when MCC opts to send Sophia to the SHU and lock her up in solitary confinement for protection, rather than hiring better guards and punishing the attackers.

14. Piper Lies For Alex, Alex Betrays Her

When Piper finds herself sent to Chicago to testify against Alex’s old crime boss Kubra, and Alex begs her to lie on the stand, which she does, but then Alex betrays her and tells the truth. That was quite a tough moment to fathom because you want them to be unified, but perjury is a crime so…

13. Humphrey is a real garbage person. There are Bond villains with more human decency than this guy. When he made Suzanne and Maureen, who had been in love previously, play Fight Club, which ended with Suzanne decimating Maureen’s adorable face, that was definitely one of his more horrible moments.

12. The episode where Ruiz’s husband visits for Mother’s Day, but on his way out he tells her that he thinks it’s a bad idea for their daughter to grow up visiting her mother in prison. This bombshell hit heavy and we all sobbed along with Ruiz.

11. The Compassionate-less Release

There are many older ladies in Litchfield, and when one of them, Jimmy Cavanaugh, is chosen for “Compassionate Release” after accidentally breaking her arm it’s extremely bittersweet. If you don’t remember, Jimmy suffers from delusions that appear to be related to undiagnosed dementia. She gets out of prison but is left confused at a bus stop with nowhere to go and no money.

10. Brook Soso is incredibly upbeat when she first arrives at the prison, but her sunny disposition takes a turn when she’s sadistically bullied and goes to Healy for help. He offers her medication, which she only reluctantly accepts so that she can attempt suicide. Luckily, Poussey discovers her in time to save her life.

9. Getting out always feels like the goal, but when Taystee actually achieves it through parole, she finds that life on the outside isn’t as easy as she thought it would be. She ultimately decides that life in the prison is better because at least there she has friends and some semblance of stability. Watching her get a taste of freedom and not know what to do with it is heartbreaking.

8. Sofia’s Hormone Withdrawl

Sophia relies on a specific dosage of estrogen to keep her hormones balanced, but in the episode where MCC cuts funding and, without warning or notifying her, lowers her dosage, we have to witness Sophia go on a downward spiral that is truly hard to watch.

7. It’s never fun to watch one of the fan-favorite characters suffer a setback and Taystee is possibly the most favorite. When she went all the way through the “job fair” contest only to win and discover at the end that there was not an actual job to be had, that was infuriating.

6. Lorna has always been one of those characters that you can’t dislike. For all of the first season, she talked about her man on the outside, Christopher, but then in the second season, we tragically found out that her infatuation with Christopher was nothing more than a delusion that resulted in her stalking him.

5. Nicky Goes To MAX

Nicky and Red have a unique, often indefinable, relationship but there’s never been any question of their connection. That deep closeness is why it’s so hard to watch the scene when they say goodbye to one another as Nicky is dragged off to MAX. The tears flow aplenty.

4. Pennsatucky is entirely unlikable at first, but her character eventually grew on fans as we got to know more about her and her rough edges were softened. Definitely one of the hardest, most triggering moments in all of OITNB was the scene where Pennsatucky’s guard boyfriend violates her trust and forces himself on her. There may be more “heartbreaking” moments on our list, but none more equally enraging.

3. Poussey turns up on the list many times because her narrative was always taking a depressing turn in spite of her positive attitude. Her backstory was no different, as we had to watch her suffer the heartbreak of not being accepted by her teenage girlfriend’s father. Being that the man was Poussey’s father’s military commander, he has them transferred out of the country to separate the two girls. Seeing Poussey confront him by threatening his life, and then her father coming to stop her and show her acceptance is a “whole box of tissues” moment. 

2. Litchfield’s Greatest Tragedy

There is no simple or easy way to talk about Poussey’s death. It was painful to watch. You become so invested in these characters that watching her slowly be crushed to death brought helpless feelings. The aftermath, however, that’s when it got heavy. Watch the other women react and respond to what happened to one of their friends… well, that directly led to the explosive season four finale and is a running theme through the entire fifth season.

1. That season four finale is pretty much the entire number one slot, considering how many intense things happen, but it’s the flashbacks of Poussey on her final night in New York, before moving to Amsterdam, that really kicks you in the chest. You have to watch her live a life full of potential and possibility while knowing what her fate became. This one doesn’t just break your heart, it shatters it.

The fifth season of Orange Is The New Black is now on Netflix, so make sure to queue it up and have some Kleenex nearby.

More: ‘Orange Is The New Black’ Stars Explain That Season 5 Cliffhanger