Heartbreaking in Hindsight

An event which is made sadder by a later event. Differs from Harsher in Hindsight in that the events may not necessarily be bad or harsh. The events that are Heartbreaking in Hindsight might be a Heartwarming Moment and it is only until the later event that you see sadder subtext in the first one.

Compare Funny Aneurysm Moment (funny that turns disturbing or sad), Harsher in Hindsight, Heartwarming in Hindsight, Tear Jerker. Contrast Hilarious in Hindsight.

WARNING! There are unmarked Spoilers ahead. Beware.

Examples of Heartbreaking in Hindsight include:

Fan Works

In the Marvel Cinematic Universe Self-Insert Fic A Twelve Step Program to Omnipotence, Michael accidentally kills Queen Ramonda. In response, Shuri succumbs to her hatred, allies with Klaue and becomes host to the Ghost Rider in service to Dormammu in order to get vengeance. Years after the relevant chapters of that fic were released, Black Panther: Wakanda Forever came out. In it, Ramonda dies in canon, albeit by a different, deliberate attacker, and while Shuri doesn't go nearly as far as in that fic, she does end up mired deep enough in grieving, hateful vengeance that who she sees in the Ancestral Plane is not her father, mother or brother, but Killmonger.

Film

In the film Black Panther M'Baku gives a giant smile of relief when T'Challa's family successfully revives him after his Near-Death Experience, showing that he does have a soft side. In Avengers: Infinity War, T'Challa gets dusted by Thanos, along with a good number of the Wakandan forces. All M'Baku can do is stare at the battlefield with an anguished expression.
Sticking with the Marvel Cinematic Universe, Tony Stark's words to Peter Parker in Spider-Man: Homecoming of "And if you died, I feel like that's on me. I don't need that on my conscience." become that much more painful in Infinity War when Tony is helpless to prevent Peter's death from the Snap.
Speaking of Infinity War, Dr. Strange is genuinely grateful for Tony and Peter coming to rescue him from Maw. They proceed to work together to stop Thanos, complete with teaming up with the Guardians of the Galaxy. The relationship between him and Peter proceeds to sour in Spiderman: No Way Home when Peter accidentally botches Dr. Strange's attempts at a spell to help him.

Live-Action TV

In The Good Place season three finale, "Pandemonium," Chidi and Eleanor talk about the fact that he has chosen to wipe his memories, and their blooming relationship, . Eleanor puts on a brave front while crying on the inside and later the outside, but Chidi reassures her that they found each other before, and have all of Jeremy Bearimy to spend time together once they complete this experiment. He's able to keep this promise towards the end of Season 4, but the series finale reveals that he is ready to enter the final door before Eleanor is, and she tearfully has to let him go for his happiness.

Western Animation

BoJack Horseman could make a drinking game out of these moments. We advise you don't, because it may lead to alcohol poisoning.
- The second episode ends with Diane, BoJack's ghostwriter, encouraging him to open up about his real childhood, not the saccharine lies that he's obviously painting, to make the book better. Since this it the first time in a while that someone wanted to know the real BoJack and pushed past his barriers -- Princess Carolyn knows better than to probe the horse, and Todd is simply happy to provide emotional support for a friend-- he proceeds to open up to her, as she takes notes on paper. The ramifications of this decision play out over the next few seasons: BoJack is very hurt and insulted when he reads her biography of him, titled One Trick Pony, that includes all the embarrassing stories that he told her. He later points out to Diane in "Hank After Dark" that she never apologized for hurting his feelings but wants him in her corner and in season five he says the book made him feel better about himself and the terrible things he did. That's not even going into the crush he develops on Diane, who is in a committed relationship with his Sitcom Arch Nemesis Mr. Peanutbutter; the first sign that BoJack has truly taken a step forward is when he refuses to act on that crush at an opportunity where there would be no legal ramifications if he had given into temptation.
- Season four ends with BoJack getting a happy ending of sorts, where despite what happened with Hollyhock, she makes it clear she doesn't blame him for a senile Beatrice spiking her coffee with amphetamines and causing Hollyhock to overdose. Even though it turns out that BoJack isn't her father, they find out their half-siblings, and Hollyhock says shyly she's never had a brother and always wanted one. When it seems BoJack will derail this positive step forward in season 5, he manages to not alienate her. Then "The Horny Unicorn" happens: Hollyhock sents a letter to BoJack that causes him to start drinking again after a few months of sobriety, and she disconnects her phone. It's strongly implied that she severed ties with him.
The Owl House
- Luz becomes thrilled when Eda accepts her offer to become an apprentice and stay for summer break, rather than go to summer camp. She lies to her mom via text. She wakes up nearly the next morning looking for witch clothes. Then Dr. Noceda finds out the truth during "Yesterday's Lie" when Luz blows her cover story to save Vee, and she breaks down. She asks if Luz gave up her life on Earth to pursue a "witch fantasy".
- Eda tells Luz that the reason they stole a paper crown from the Warden was to make King happy because she and King are the only family that each has. This leads to a lot of moments where we find out why Eda is estranged from her family, including that her own sister is hunting her down to make her join the Emperor's Coven. Then of course King has a breakdown when he learns the truth about his origins in season two; that is, that Eda rescued him from what she thought was a robot monster on a deserted island, and she accidentally planted the idea of him being a king while commenting on how he played with his toys. Eda apologizes to King for leading him on, saying that she didn't want to break his heart by admitting she doesn't know who or what he is.
- Eda saves Lilith from a spider monster during "Sense and Sensitivity", jokingly saying that she's the only one allowed to kick her big sister's butt. Then the season one finale happens, where Eda fights Lilith more seriously to rescue Luz, and comes close to mauling her in Owlbeast form when they're locked in a petrification cage together.
- Luz finds a kindred spirit Philip Wittenbane when reading his journals, as another human that explored the Boiling Isles. She affectionately tends for the Echo Mouse that can play back his journal entries. Then she meets the guy in-person during a time travel run with Lilith, who proceeds to use her and Lilith as a sacrifice to secure an ancient artifact. Luz can't believe he's actually a big jerk, and apologizes to Lilith for trusting him. She doesn't even know that he's Emperor Belos, four hundred years older, until he reveals himself in "A Hollow Mind" and breaks Luz.
The show Tuca & Bertie has quite a few:
- In a heartwarming moment between Speckle and Bertie, where Speckle creates a romantic roleplay for Bertie after she admits, following an episode of miscommunication, she wants to add some surprises to their sex routine. They end up reviving the spark between their relationship. In the season one finale, Speckle calls out Bertie for refusing to answer her calls for a week, and was worried that something had happened to her. He says that he can't be the rock in their relationship to constantly provide emotional support or automatically knowing her needs. They do make up, but Bertie admits that she has a lot of work to make up for ghosting Speckle, to be his rock.
- When a sloshed Speckle witnesses Tuca taking emotional abuse from her aunt, he whispers for her to stand up to the lady. Later, he comforts Tuca that You Did the Right Thing by tearing up the woman's check after her aunt belittles her single mother. In the season finale, Tuca finds out that her aunt is in the hospital from cirrhosis, and their last conversation was a huge fight.