Eloise admits in a private moment with Daphne that she acts like a jerk about marriage because she's scared of having kids. Namely, she recounts the night their mother nearly died having Hyacinth, mere months after they lost their father. She and Daphne were closer at the time, and Daphne tried distracting her from the screaming while singing. Eloise acknowledges that she appreciated Daphne's attempts to comfort her, but she still has nightmares about their mother screaming. This gets Daphne to admit that she remembers that night all too well.
After a season of emotional turmoil, Anthony finally wishes to be seen with Siena in polite society — though he invites her to Daphne's ball, at the last minute she refuses. She's tired of being kept in the shadows and knows she'll never be accepted in Anthony's world; and while it's clearly been an incredibly hard decision for her to make, she's decided to end their relationship and move on while tearfully urging Anthony to do the same.
Lord Featherington breaking down and sobbing hysterically that he does not know how to fix what he’s done after Portia calls him out on his gambling away their fortune and their daughters’ dowries.
Simon's entire childhood. His mother died in childbirth and barely got to so much as see her child before dying, and his father outright rejected him for having a stutter. No matter how hard the little boy tried to improve himself and impress his Papa, even excelling in other aspects of life such as academics, the old monster never loved or accepted him due to his simple stutter. In fact, he outright tells him he's a mistake and a stain on his family honor when he was eleven years old. It's devastating to see Simon twisted into an emotionally remote and self-hating rake because his only parent cared more about his legacy than his own son. He's even willing to destroy his own chance at happiness with a woman who loves him flaws and all... just to spite a man who is long since dead.
Of course it doesn't stick, but Simon breaking things off with Daphne just as they both start to realize they genuinely care for each other. It's clear he's forcing himself to say things he doesn't believe, out of a real desire to ensure she doesn't harbor anything but disdain for him. He can barely maintain eye contact with her the whole time. They're both left broken, bitter, and saddened by the end of the episode.
Penelope breaking down in Eloise's arms at the end of episode 6. It becomes even worse because by the end of the season, the viewer realizes she was not just crying because her family's reputation was destroyed, but because she is the one who destroyed it.
Marina Thompson's whole plotline. All she did was fall in love but it all went horribly wrong.
In "Oceans Apart", Colin telling Marina that if she'd been honest with him, he would have married her without hesitation.
The news of Lord Featherington's death. He may not have been the best husband or provider, but Portia breaks down in his office upon realizing what his death means for her and her daughters.
Penelope is later seen bawling in Eloise's arms, overwhelmed with grief. We may not have seen Lord Featherington interact with his daughters on screen much, but to see Pen so devastated by his loss seems to suggest that she had fond memories of him, which makes it all the more heartbreaking for her.
Season Two
While it's still fairly lighthearted in season two, Eloise's Performance Anxiety when she's expected to present herself to the queen is poignant. She stalls on showing her family her outfit because it looks ridiculous, not ladylike at all, and begs her mother to let her get out of her pithy attempts to impress the queen. Much later, when she practices dancing, she's still nervous about the fact that she can't measure up to Daphne's season. It comes to a boiling point when she runs out of a ball and tearfully apologizes to her mother for being a disappointment, causing Violet to realize she was pushing Eloise too hard.
There's something utterly devastating about Anthony's panic attack when Kate is stung by a bee. For all he's railed against it, he is already so much in love with her that the prospect of losing her (the same way he lost his father, as if it wasn't bad enough already!) is enough to utterly wreck him.
Kate's backstory: through no fault of her own, she's the most scandalous item to arrive to London. Her mother, a noblewoman, married a clerk, and by all accounts, they had a happy life in Mumbai. Then her dad died, and his income stream, plus any savings that Mary had, dried up over the years. Kate knows that the queen looks down on her as living proof of what her stepmother fled from London, and her step-grandparents treat her as an annoyance. While the Sheffields will financially support them if Edwina marries a nobleman, Kate doesn't want Edwina to be forced into an arrangement. She wants her little sister to find love and happiness, something she feels she doesn't deserve to have. Lady Danbury has to call out Kate, saying she deserves better than to be a neglected old maid.
Edwina's outrage once she realizes that Kate and Anthony are in love is overshadowed by the sheer pain the girl is in. She has trusted Kate implicitly her whole life, believing everything she does is to help her, and now is faced with what is to her mind absolute betrayal. She's not just spitting mad after she bolts from the altar, she's choking on tears and very close to a nervous breakdown. For her part, Kate can do nothing but stand there and absorb her sister's fury, knowing that she is guilty of it all and the relationship they cherish is forever ruined.
The nadir occurs a few scenes later, when Kate refers to Edwina as "sister" and Edwina immediately snaps back, "Half-sister". The anguish that one word, that single distinction causes Kate is heartbreaking.
Kate's stepmother assuring her that she was never anything less than a full daughter to her, and admitting she shouldn't have let Kate take on all the burdens for their family after her father died.
Kate: You took me in as your own. And you never treated me any differently. Everything I... I did, I owed it to you. Lady Mary: You owed me nothing. Oh... You never had to earn your place in this family. I loved you from the day I met you. Oh, love is not something that is ever owed. You came into my life as a daughter, and I never saw you as anything else. It grieves me to think you do not believe you deserve all of the love in the world.
The flashback to Edmund Bridgerton's death. He dies randomly on a sunny day, stung by a bee while gathering flowers with his son after spending the day together. One moment, everything is bright and happy. The next, he's dying. He's gone within minutes, leaving his son and heavily pregnant wife to watch in horror as their world crashes down around them. Going by his symptoms (a nasty rash developing where he was stung, and severe trouble breathing), it's pretty clear that he had an allergic reaction.
A blink-and-you’ll-miss-it tearjerking detail: The flowers Edmund had stopped to pick when he was stung were hyacinths.
Later, Kate being stung by a bee. She's completely fine, more annoyed than hurt, but Anthony is visibly freaking out, asking if she's alright and clearly terrified someone he knows is going to die in front of him again, the exact way his beloved father did. When Anthony later tells her how Edmund died, Kate is visibly affected when she understands his reaction.
Just the fact that Anthony never got the chance to truly grieve his father before he had to take his place. Immediately after Edmund dies, Anthony is bombarded with the need to make arrangements as the new head of the house. The worst of it is the night that Hyacinth is born, and the doctor tells him that he will have to choose between saving his mother or his sibling. Of course we know that Hyacinth and Violet both make it out fine, but it's gutwrenching to watch Anthony struggle to even speak while his mother screams that Edmund should be there, not him.
The flashback to Violet immediately after Hyacinth's birth. She's nearly catatonic, forcing herself just to keep living day by day. This is what puts Anthony off of the idea of ever marrying someone he loves, terrified that he could inflict such agony on someone if something should happen to him.
Immediately after this flashback, in the present, Anthony goes to visit his father's grave and Violet finds him there. She tries to talk him into marrying for love by citing her marriage to Edmund and how happy it made her...only for Anthony to throw it in her face (albeit calmly) by informing her that her breakdown over his father's death and how much she loved him is why he never wants to marry for love. Her shocked and regretful expression says it all.
In the midst of an already terrible situation at the failed wedding, King George wanders in... thinking it's his and Charlotte's wedding day. Charlotte is obviously devastated, while he affectionately calls her "Lottie" and babbles about how excited he is about the wedding. Some guards come to escort him away, but he fights them and asks why they're doing this, obviously distressed, while Charlotte watches in agony. Luckily, Edwina plays along, showing him kindness and calming him down, before gently persuading him to go and rest.
At one point, Daphne mentions that Anthony never wept over their father's death, despite how traumatic it clearly was for him. Later, when he hears that Kate survived her accident, he finally puts his head in his hands and cries. It feels like a very long time coming.
The confrontation between Eloise and Penelope over the Whistledown papers.
Penelope:[crying] Eloise, I'm sorry. I'm so sorry. You are right about all of it. I was trying to protect you. Eloise: Is that what you were doing?! By writing about me in your latest sheet?! By telling the entire world about things I trusted you with?! Penelope: Only to convince the queen it wasn't you. It was the only way I could save you. Eloise: The only person you were interested in saving was yourself. All so you could keep making money, at a cost to everyone else. At a cost to Miss Thompson. To my brother. To my entire family. To your entire family. I ended my friendship with Theo because of you! One of the only good things in my life, all because of your self-serving manipulation! Penelope: You have no idea how horrible it has felt to keep this from you, from everyone, for so long! Whistledown has been all I have had, and I have given it up. I am done with it. I wrote what I wrote, and I gave it up for you. Eloise: I do not even know you. I look at you now, and all I feel is pity for you. Sequestered here in this very room, writing your secret little scandal sheet, tarnishing everyone in town because you are too scared to stand up for yourself in reality. You are something, Penelope. An insipid wallflower, indeed. [walks to the door] Penelope: At least I did something. All you ever do is talk about doing something. You've all these great ambitions, these great plans, but I am the one who did something great, and you cannot stand it, can you?! And what do you think that makes you? Eloise: I wish never to see or speak to you again.
Season Three
The season begins with Eloise still denouncing Penelope. Worse, she's associated with Cressida. Penelope is devastated upon finding out that her former best friend is now with her worst enemy who has bullied her for two years.
With all she has been through, something has been broken in Eloise. She has shut off her interest in freedom and now cares only for doing exactly as every other girl in the ton is doing, finding a husband and going through the motions.
The introduction of Lord Kilmartin. It may not seem like a sad moment, but anyone who has read the books almost certainly had a feeling of dread for him and Francesca upon realizing who he was.
After Lord Debling retracts his proposal for Penelope and leaves her humiliated and near tears, Portia's first reaction isn't to comfort her upset daughter. Instead, she immediately demands to know what Penelope did to cause him to leave. A hurt Penelope demands, "That is your question? Not am I well? Do I only matter to you if I have a lord’s engagement ring on my finger?"
After Portia reads about Penelope's engagement (from a Lady Whistledown edition), she isn't happy to hear her last single daughter is marrying into a wealthy and respected family. Her first thought is to criticize Penelope for choosing to marry a man she believes to be out of her daughter's league (and from a family they have a bad history with) instead of a more "sensible" match like Lord Debling. She even accuses Penelope of "using her wiles" to entrap him before Colin angrily barges in, having stopped by and overheard. He states he proposed out of love and defends her to Portia. Later, Portia says she had no idea it could have been a love match. It never occurred to her that someone could marry her daughter out of simple love for her.
After taking her away from the scene, Penelope is moved to tears and tells Colin how no one has stood up for her like that before. When Colin tells her he loves her, Penelope responds, "Are you sure?" She has spent so many years being mistreated as The Un-Favorite by her family that she doesn't believe anyone can genuinely love her.
Colin finding out Penelope is Lady Whistledown. The two had been in full, romantic bliss after getting their Relationship Upgrade and were deliriously happy as they neared their wedding day. And now all of that's been destroyed by The Reveal of Penelope's secret identity. He's left in full tears of fury, heartbroken to find out the woman he loves is also the person he deeply loathes due to the societal damage she's caused his family. He says how he knew she was keeping something from him, but never this. He asks if she's truly been Lady Whistledown all along, to which a guilt-ridden Penelope can only nod. He takes a step back in shock and when Penelope tries to explain herself, he refuses to hear it as he lists out the hurt and lies she's inflicted upon him and his family. He declares he will never forgive her and angrily storms off as she cries.
What really adds to the hurt is a few things. First; Colin found out by following her to the printers on the rough side of town. He admits he only followed her because he was terrified her carriage driver had abducted her. Instead, he ends up overhearing that she's the gossip writer who's nearly ruined his family multiple times. (Even if her intentions were good.) Second; he assumed that the secret Penelope was hiding was that she didn't actually return his love for her. His insecurity led him to believe she only went along with his Anguished Declaration of Love out of nothing more than simple Lust and she was just going along with things now.
Also, Penelope only decided to print again (when she planned to retire her business) because (once again) she only wanted to protect the Bridgerton family when finding out Cressida was going to take over the column and was likely going to slander them. (Which she does and it's only Penelope's column that saves them from potential ruin.) She only wanted to do something good with her social power over the Ton and protect the family she loves like her own—and it led to Colin finding out her secret and drives a deep wedge between them.
Seeing Penelope and Colin's marriage start off rough due to her Lady Whistledown secret. They manage to have an overall happy wedding and even share a beautiful Dance of Romance and things start to look positive... until Queen Charlotte barges into their wedding and gives him a harsh reminder of the burden Penelope's secret carries. This isn't helped by Penelope refusing to give her column up. After this, they begin to Sleeping Single and have a frosty atmosphere around them. While they quickly work things out and end the season Happily Married, it doesn't make this brief rough patch between them hurt any less.
Despite her rotten behavior, it is hard not to feel a little sad for Cressida at the end of the season. Her final scene is her in a carriage with a defeated look on her face on her way to live with her horrid Aunt Joanna. Yes, she attempted to blackmail Penelope (and has been an Alpha Bitch)—but it was in a last-ditch attempt to restore her ruined reputation in Mayfair and escape her toxic family, not to mention a nightmarish marriage to a man several decades her senior.
Colin's appeal to her decency seems to be softening her...until he spouts some nonsense about the love of family, naively thinking Lord Cowper will welcome Cressida back on this basis. She has never been able to count on her family's love, least of all her reptilian father's, and Colin's clumsy attempt to connect with her only reinforces how little he understands her struggles.