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.

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.

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 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 . When it seems BoJack will derail this positive step forward in season 5, he manages to not alienate her. Then "The Horny Unicorn" happens:.
 * 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.