So much of Eleanor's life is this. Her parents were a pair of selfish jerks who hated each other and cared nothing for their daughter, driving her to emancipate herself from them when she was just fourteen. She also had very few friends, and the few friendships she did have either weren't really close or were utterly toxic, with the few decent ones (such as her ex-boyfriend Sam) having ended largely because she pushed them away to avoid being hurt. On top of that, she dies in a very meaningless and embarrassingly painful way and ends up in an afterlife where her fears of being looked down upon and hated for who she is are forced upon her as a constant reminder of her life on Earth.
Chidi's life was also pretty sucky. Throughout his whole life, his paranoia and indecisiveness led to him losing so many friends, one of which genuinely considered himself to be his closest friend from childhood. His fears led to his rather embarrassing death and now he's in a world where he's forced into an intolerable situation where he has to lie and is forced to make difficult choices that sometimes go against his ethics. His hell is literally a world of Paranoia Fuel.
Tahani had to deal with always being in her sister's shadow to the point that her many genuinely impressive achievements were always ignored in favor of Kamilah's, and their parents didn't care about her to the point they misspelled Tahani's name in their will. Even in Tahani's test given by the Judge, where everyone is implicitly talking about her, she falters and goes into her parents' room, and still, all they have to talk about is Kamilah.
As much of an idiot as he is, you do have to feel a little bad for Jason. He legitimately had dreams and goals and did want to do something with his life. His stupidity and impulsiveness were just what did him in. Now, he's stuck in a place where he has no friends (even the others don't really like him that much) and is forced to pretend to be a silent monk to survive.
"Chidi's Choice": The flashback where Chidi's lifelong best friend Uzo tells him, "It is literally impossible to be your friend." Made worse by the fact that this is the last thing he, or anyone, ever said to him. Chidi dies not even thirty seconds later. It's capped off with Uzo looking in shock and saying Chidi's name in a shaking voice just barely above a whisper.
"Mindy St. Claire":
The flashback to the day Eleanor emancipated herself from her parents when she was only 14. They don't even care that she's doing this, and the fact that Eleanor is so nonchalant about it drives in how awful they were. The ending scene to the flashback is her eating her birthday cake by herself.
At the end of episode, Eleanor explains to Jason that they can't abandon their friends and let them take the fall and admits that she'd been using her cruddy childhood as an excuse for her behavior and refusal to change when other people suffered worse and didn't turn out like she did, so it's time to own up, save their friends, and face the consequences.
"Dance Dance Resolution": The main characters have undergone over 800 different attempts by Michael trying to keep them from realizing they're actually in the Bad Place so they can continue to torture one another. Each time, their memories are erased, so the friendships and romances they forged are forgotten. It's especially hammered home when Eleanor sees the recording Mindy took of her and Chidi confessing their love for one another, but since this was in a previous reboot, she is utterly shocked at what she sees.
"Team Cockroach" shows that Tahani died trying to pull down a statue of her sister. The worst is her last exchange with Kamilah, yelling about Kamilah always hogging the spotlight and Kamilah fires off that Tahani is just embarrassing herself, as she always does.
Tahani: So is that what you think of me, that I'm an embarrassment?
Kamilah: Honestly... I don't think of you at all.
Eleanor's flashbacks highlight how messed up her life was.
The callous way Eleanor's mother Donna tells her how her pet dog died (which was Donna's fault, due to her leaving the poor animal locked up in the car on a hot day), and then telling Eleanor not to get sad over it because she didn't want to deal with it. Eleanor couldn't have been older than eight years old at that time.
Eleanor's father's funeral. She's conflicted over how to feel, as Doug was a terrible father and a lousy person in general, but the fact that he's dead isn't exactly something that brings her any happiness. And then Eleanor's mother drunkenly bursts in. More subtly tragic is the appearance of Eleanor's boyfriend Sam, who cares enough about her to support her at the funeral, and clearly sees how Eleanor became who she is. Unfortunately, despite getting past at least a few levels of her shell, she will have inevitably driven him away between the funeral and the start of the series.
Eleanor's breakdown in the flashback where she's shopping. While it is comical, it shows how much she has longed for a normal home and family. The fact that the scene takes place soon after her dad's death makes it worse.
Eleanor:(increasingly tearful) So, the parent toothbrushes can be close to the kid toothbrushes, and watch over them, and they can talk about their toothbrush feelings? And hold their little toothbrush hands when they're sad, and make sure no harm ever comes to their little bristles?
The entire plotline with Tahani being tortured by having the party she throws get overshadowed by the one Winston is throwing is largely played for laughs... until the end when Tahani breaks down and cries because even though she knew the whole time it was a ruse designed to make her feel bad, it still worked, and she doesn't like what this implies about her as a person.
Tahani: I really thought I could throw a better party than a magical, all-powerful being. And moreover, what does that say about me, about the life I lived? The way they're torturing me is through event planning mishaps...(voice breaks) ...and it works! Am I really that shallow?
"The Trolley Problem": Michael is a jerk to Chidi throughout the episode making him go through various horrific scenarios. Chidi thinks he's just being evil, but Eleanor acutely pinpoints his behavior — he's lashing out because he's insecure over his inability to grasp the behavior of humans. He's a demon and as such he knows exactly what warrants eternal torment, and as an immortal demon, he's never had to think about this before.
"Janet and Michael": Any time Janet is unhappy over Jason and Tahani's relationship. Seeing the perpetually upbeat and cheery Janet in tears is both unsettling and very sad.
"Best Self" has the last shot of the heroes leaving on the train as the neighborhood dismantles itself into nothing, meaning everything we've seen from all previous episodes is now just gone.
During the goodbye party for the neighborhood, Chidi and Eleanor dance together, which is incredibly sweet... but Eleanor loves Chidi so much, but is convinced he doesn't love her back—and is trying to be okay with that.
"Rhonda, Diana, Jake, and Trent": Michael solving the Trolley Problem by sacrificing himself. "The actual solution... is to sacrifice yourself. Look after the others. They need you."
Tahani's test in the episode is to walk through a hallway of doors labeled with various celebrities and others who are all talking of what they really think of her. She nearly makes it... but then goes through the door with her parents behind it. The talk has Tahani finally realizing that nothing she did was ever going to be good enough for her parents to love her as much as her sister. Worse, she failed the test as she had to let go of what held her back but instead embraced her inner anxieties.
Tahani: I was never going to be enough for you. Never going to earn your respect. [...] I'm sorry we didn't have a better relationship, and I wish you both the best.
Tahani wrestles with herself to go in or not, knowing that it's a trap. She gives a little groan before going in and forfeiting her win.
Worse is that during the conversation with her parents, they tell her that Kamilah dedicated her last album to her — or rather, Kamilah dedicated her last album to her fans, and Tahani's one of those, right? When Tahani briefly thinks the album was for her, she just lights up, visibly wondering if maybe Kamilah really did care after all. As terrible as their relationship was, Kamilah was still her sister; such a gesture likely would've meant the world to Tahani.
After Chidi, Tahani, and Jason fail Gen's test, the group takes the time to confess held-back feelings and say last goodbyes. Janet talks about and sorts through her lingering feelings for Jason, which gives Chidi the courage to kiss Eleanor and affirm his feelings for her.
"Somewhere Else": Eleanor's Time Passes Montage is initially hopeful as she gets her act together. Her slow decline back into selfishness is heartbreaking, and the music, "Maybe" by The Submarines, doesn't help.
One thing is sure - I'll always love you And if you should go I will pretend That I never needed you or anybody Never wanted to call us just friends So maybe, maybe, maybe we're strong But maybe, maybe, maybe we're wrong
"The Brainy Bunch": Trevor's attempts to drive the humans apart almost succeed in getting Chidi to second-guess about the group socializing and says he shouldn't be with them because it "interferes with the study". Eleanor is clearly hurt, and she says that not only did she prefer the one-on-ones with Chidi, but Chidi was the reason she flew from Arizona, not anyone else. Chidi is still not convinced, but the next day, she skips class and Chidi has to go to her hotel. Eleanor is ready to fly back to Arizona.
"The Snowplow": After Eleanor embarrasses herself by going on an angry rant, she runs into Simone outside and asks why she's like this. Simone gives a flippant burn, but Eleanor reiterates, she really wants to know, what is wrong with her? It's clear that she's reached rock bottom.
"The Ballad of Donkey Doug": There's something quietly tragic about how quick Jason gives up on saving his dad from the Bad Place. Even he can recognize that his dad can't be trusted and decides to focus his energy on saving his best friend instead.
"A Fractured Inheritance": As a counterpoint to Jason's dad being irredeemable, Eleanor's mother Donna has genuinely changed and become a better person. This makes Eleanor distraught and jealous because she wanted her mom to be better when she was a child, and even after they reconcile, Eleanor still can't fully forgive her parents for how they screwed up her life. Eleanor even spends much of the episode in denial that her mother had changed since believing otherwise would mean accepting the fact that Donna was always capable of change but never saw Eleanor as someone worth changing for.
The moment when Eleanor splutters this out to an Innocently Insensitive Michael, who asks why she can't believe that Donna is now a good mom. Eleanor with teary eyes shouts, "Because I wanted that mom!" and talks about how Donna made her look for loose fries in fast food ball pits for afternoon snacks. Michael looks extremely guilty as he realizes how much this must hurt Eleanor, and he has nothing comforting to say.
In the same episode, Tahani realizing that her sister's paintings are all about their parents pitting them against each other for their entire lives. Each painting has two large, unified objects in the middle... and two little objects sitting all alone in separate corners.
Tahani: Kamilah's work has been mediocre for years. Mother and Father are probably rolling over in their cryogenic chambers. Chidi: Really? You don't think they would be proud of her for having a whole museum wing dedicated to her work? Tahani: My parents' standards were incredibly high, and they were impossible to please. Plus, they always pitted my sister and me against each other. The two of them were a unit, and Kamilah and I... (Tahani trails off as she stares at the paintings, suddenly understanding.)
Kamilah's face when Tahani wraps her arms around her and tells her she finally understands. In all these years, this might be the first time Kamilah ever truly saw her older sister.
"Don't Let the Good Life Pass You By" has Michael and Janet meet Doug Forcett in person, and it turns out his miraculously accurate vision of the afterlife during a drug trip has caused him to spend the rest of his life terrified of doing anything that could jeopardize his chances of getting into the Good Place. He's become a complete and total Extreme Doormat who'll do absolutely anything at his own expense to try to put more good into the world no matter how miserable it makes him, to the point that Janet describes him as a "happiness pump". Worse, by the current point system, he'll end up in the Bad Place anyway even though his points aren't invalidated as he doesn't unequivocally know that's how the system works.
To a lesser extent, the fact that the humans are dead again. Kamilah and Tahani buried the hatchet and then shortly after, Tahani dies again, in circumstances Kamilah could never understand. Similarly, Pillboi and Donkey Doug no doubt had to feel hurt at Jason's passing, especially since the latter is Jason's father.
The Reveal in "Janet(s)" that no human has made it to the Good Place in over five centuries is both horrifying and tragic. Millions of otherwise decent people have been sentenced to eternal hellish torture all because of the points system being so flawed by taking into account of the unintended consequences of even the smallest seeming actions that most people wouldn't even consider...
While it's mostly Played for Laughs, Matt the accountant's situation is just awful. The poor guy has the job of having to review all of humanity's weird new sex acts and it's driven him to utter misery, to the point that he regularly asks his boss for permission to kill himself because he just can't take it anymore.
The majority of "Pandemonium" is achingly sad. The Bad Place picks Simone as one of the human test subjects for the new fake Good Place experiment. Chidi insists he won't be able to keep his cool around her, and the only solution is to wipe his memory back to right after he died, which would erase his relationship with Eleanor in the process. Michael gives them a sweet send-off with a clip show of their moments together, and both members of the pairing are crushed to the point of tears. Eleanor then suffers a Heroic BSoD and asks Janet what the answer is, and why life and love hurt so much. Only after Janet's support can she go welcome the mind-wiped Chidi.
Michael's breakdown as well. Eleanor has to take over as the architect after he becomes crippled by his anxieties, which were caused in part by Shawn sadistically promising to torture Eleanor, Chidi, Tahani and Jason with demons dressed as Michael himself.
"A Girl From Arizona, Part 1": In the opening scene, you can almost hear Eleanor's heart breaking when Chidi says he forgot her name.
"A Girl From Arizona, Part 2":
Eleanor has a breakdown with the high stakes of the experiment, crying about the general hopelessness of the situation and capping it off about how she's only a girl from Arizona, and Michael gives her a pep talk about how she beat him repeatedly and is the only one who can save humanity.
Janet tells Jason that she thinks it's best they "take a break" so she can concentrate on her new duties, which clearly affects him. She then has to break it to Jason that Blake Bortles was cut from the Jacksonville Jaguars. The combination of bad news makes it look like Jason has lost all hope in going on at all.
Eleanor making the tough call to tell Chidi that Simone is his soulmate to get her to stop acting like the afterlife isn't real.
"Chillaxing": Eleanor and Michael decide that Chidi isn't helping the other test subjects enough because he's too happy, so they come up with ways to trigger his anxieties by "revealing" Jason. Chidi eventually comes to Eleanor's office and confesses that he's unhappy in the Good Place because it feels like the universe is punishing him, which causes her to break down in tears from the guilt of torturing him and, as she previously admitted it in a Jerkass Realization moment, secretly enjoying getting to vent at least a little of the hurt, anger and betrayal she felt by Chidi choosing to have his memory wiped (which included the relationship he'd built with her).
"Employee of the Bearimy"
Michael finally confirms that demons aren't fundamentally evil. On the contrary, Shawn reinforces they are providing balance in the universe and every demon who tortures is valuable. Now he knows Shawn is a Consummate Liar who just wanted to torture. Michael is regretful that he bought into such bull-shirt and enjoyed torturing people who didn't deserve it.
Janet's situation: she's trapped in the Bad Place and regularly taunted by Vicky in a Michael suit. While it's a No-Sell on Janet because she knows Michael, when the real Michael and Jason show up she's just irritated and hurt on seeing a new form of torture. The way her face lights up when Jason confirms that he's the real Jason shows how much the situation was emotionally draining.
"A Chip Driver Mystery"
Bad Janet's situation until Michael frees her: she's imprisoned in a special holding cell in our Janet's void where there's nothing to do but fart in the face of her visitors. While it's better than being locked in Mindy's house, Michael acknowledges that it's cruel and he doesn't want to keep her locked up forever.
Brent, due to his utter lack of humility and self-awareness, inadvertently putting the experiment in jeopardy.
"Help Is Other People"
Chidi says he hopes that Eleanor didn't lie about Simone being his soulmate. Simone logically points out there's no rational reason for that to be true. You can see him looking crushed on the inside.
Simone breaking up with Chidi because they don't agree on saving Brent. Sure, Both Sides Have a Point, but neither of them deserved having broken hearts.
Chidi's situation at the end of the episode: his girlfriend broke up with him and bailed with his other friend, and he's stuck in what he thinks is the Bad Place with the one person he hates. Though it makes his Defiant to the End attitude towards Eleanor, Michael and Brent so awesome because he has grown so much.
Eleanor is so stressed about not knowing how the experiment went that when Janet brings margaritas, Eleanor forgoes the glass and chugs the entire pitcher.
The heroes have made it to Good Place, for real this time... but it turns out even that's not all that it's cracked up to be. The human residents there have grown bored and miserable from eternal paradise and many of them have lost their minds, to the point that Eleanor describes them as "happiness zombies". The titular character herself, Hypatia, has lost her zest and can no longer wrap her mind around the things that she was passionate about in life until she meets Chidi, who offers her a new challenge.
The revelations in this episode definitely cast a new light on the Good Place Committee as well. After all, their whole purpose for existing is to make humans happy, but they can see that their methods of giving these people everything they could ever want and then some isn't working anymore. They're just as trapped by the system as Shawn (who admitted to growing bored with the repetition himself).