A badass falls head over heels in love and has their heart broken, sometimes because their love interest outright rejects them, sometimes because the object of their affections falls in love elsewhere or is already in a relationship with another, or some other tragic event happens that denies the badass the affections of their love interest. The worst case scenario by far is when their love interest is Stuffed into the Fridge, killed off just to spite the badass.
- Hamato Yoshi of Teenage Mutant Ninja Turtles in various continuities, including the second animated series. He loved a woman named Tang Shen who ended up being murdered.
- Marv of Sin City. His only starring role in a full length story starts with him discovering the first woman to ever sleep with him has been murdered. Seeing how he normally responds to violence against women and violence against friends.... you get the idea.
- Spider-Man: Spider-Man lost Gwen Stacy to the Green Goblin. It's one of the most iconic moments in his history but damn, poor Peter. Meanwhile, in stories set in the future/Alternate Universes/What Ifs, it's common for his most famous love interest, Mary Jane Watson, to die or disappear. (Just see the page image with Spidey doing a Cradle of Loneliness on Mary Jane's headstone.)
- Supergirl: In Young Love, Dick Malverne, Pre-Crisis Supergirl's childhood crush died after confessing he loved her and he knew her Secret Identity all along, leaving her heart-broken.
That was the last time I saw Richard. He died later that night. I couldn't save him. I couldn't save him. Richard was right about real strength, though. It is on the inside. And I know I'll find it. Just not tonight. Tonight I know what it is to be human. Tonight my super skin is still invulnerable, but my Richard is never coming back, and my heart is broken into a million pieces.
- Cyclops from X-Men has lost Jean Grey twice (and He's often misblamed for her loss the second time around). He also lost his first wife, Madelyne.
- Spawn: The titular main character made a Deal with the Devil just so he could go back to earth to see his wife Wanda again, and what does he get to see? Wanda - happily married to his best friend in life and with a daughter. Ouch.
- Royals: Ronan the Accuser, in addition to the complete annihilation of his homeworld, is also distraught over his forced separation from Crystal, to the extent it's all he accuses her of when putting the Inhumans on trial. As Crystal points out, that situation was kind of his own damn fault.
- In Robin Tim's longtime girlfriend Stephanie Brown was tortured to death by Black Mask, to make matters worse this happened right before his father and two best friends were killed, all of which combined caused a drastic permanent change in his personality. Stephanie's death was eventually retconned to have been faked so she was able to return and, after a lot of discussions about trust and betrayal, they resumed their relationship.
- In Thousand Shinji, Asuka's death broke Shinji down completely, up to the point of losing hope for first time in his life.
- Children of an Elder God: Misato was pretty heart-broken and hurt after her boyfriend Kaji's death.
- Ghosts of Evangelion: After Asuka's death, Shinji is so heart-broken than he loses his will to live.
- In The Second Try, when Unit-02 blew itself up during the Final Battle, Shinji believed that Asuka was dead. He was so heart-broken that he almost ended humanity again.
- In Neon Genesis Evangelion: Genocide:
- Shinji was heartbroken when Asuka was in a coma and he couldn't do anything to help her.
- And later on, when Asuka was dying, he was completely broken. When he realized that she couldn’t answer when he talked to her, he felt his heart breaking.
And in that silence, Shinji felt his own heart falling apart.
- Last Child of Krypton:
- After the battle against Zeruel, when Shinji was supposedly killed-in-action, Asuka fell apart.
- In the rewrite, when Shinji was mortally wounded, she was so grief-stricken that she ran out of their apartment and wandered for several hours.
- Shinji doesn't show it outwardly in Once More with Feeling, but he’s traumatized because he abandoned his life’s love when she needed him the most, and he let her die.
- In a Kung Fu Panda fic The Vow, Lord Shen becomes this when he's banished from home for his crime of massacring pandas while his parents and Lady Lianne, his fiancée, act in an outwardly cold way while doing that (in reality, they're sad at having to do it). Viewing it to be an unjust response to his efforts to prevent his fate, Shen swears to conquer China and have his revenge. Later, near the end of the story, Shen suffers a Villainous B.S.O.D. after he releases his newlywed wife Lianne out of love and ponders on how far he has fallen. It doesn't prevent him from engaging in his final confrontation with Po in the same way as in canon though. However, he survives, returns to Lianne and resigns to live with her.
- In the Jackie Chan Adventures fic The Ultimate Evil, Lo Pei is revealed to have lost his wife to childbirth and raised his son and daughter by himself under Shendu's rule. He stirred up the rebellion against Shendu only after the Fire Demon forcibly took his beloved daughter Lo Mei as bride. While Pei successfully imprisoned Shendu, he couldn't save Mei in time to stop her from committing suicide.
- Cullen gives the very strong impression of being this in All This Sh*t is Twice as Weird, when Dorian is the Bearer of Bad News that the Inquisitors, among others, have fallen into a Fade rift. He can't afford to grieve too openly, because he still has to lead the troops and doesn't want to shatter morale, but it's clear to Dorian (and the reader) that he's completely devastated.
- In Superman of 2499: The Great Confrontation, Katherine de Ka'an investigates what happened between her distant ancestors, the first Supergirl and her first husband Dev-Em. It's only known Kara's diaries stop mentioning him altogether after she moves off world, utterly heartbroken.
Dev... Dev... Dev... Kara's diaries were full of his smiles, the sound of his voice calling her name. The feel of his body and the labyrinth of his mind and heart. No, all this was plain for any and all to read. What was less clear was what happened to him.
Something had sent a grieving Kara Zor-El fleeing back to Rokyn, wounded in spirit and bleeding from the only place she was truly vulnerable: her heart. Something terrible had happened. And yet the diaries did not name the cause. Whether this was because there were parts of it missing... or because Kara Zor-El could not bring herself to speak of it was difficult to know. The only thing that was sure was that, beyond a certain point, the name of Dev-Em was never spoken.
- Manolo in The Book of Life, when it looked like Maria dies after saving him from a snake bite.
- Sgt. Calhoun from Wreck-It Ralph. She's programmed to have the "the most tragic backstory ever": Her fiancé was eaten by a bug at their wedding, which she then kills. Since the bugs become what they eat, Sgt. Calhoun had to kill a bug hybrid of her fiancé.
- The classic case is Cyrano de Bergerac; the titular big nosed master swordsman helps his rival and best friend get the girl.
- In The Phantom of the Opera, the Phantom, Erik, was one of these. One of the main examples comes at the end of Act I.
- Miss Saigon: Given that three years after being forced to abandon her in war-torn Vietnam, Chris is still having nightmares about Kim, he counts as this. His troubled marriage and Kim dying in his arms at the end of the show cinches it.
- The Mrs Hawking play series: Colonel Reginald Hawking, who devoted himself to some fairly epic military service abroad after coming to the understanding that the wife he loved couldn't stand the sight of him.
- This has happened to Brooklyn from Gargoyles three times - two in the canon TV episodes and once in the canon comic book. He finally finds his true love in his Timedancer adventures, Katana, and starts a family by the time he gets to his home time period.
- Danny Phantom had one after he was put under a love song by Ember into believe he was completely in love with Sam(antha). Though she liked the attention, even though he was going into Stalker with a Crush territory, he was unable to focus on anything but her almost causing their death several times. To snap him out of it, she kisses Dash which causes him extreme heartbreak. However, he was able to deal with this by fighting Ember.
- Razer from Green Lantern is this after Atrocitus started a war that resulted in the death of his wife alongside many others. Kilowog also lost his family and home planet, but finds another alien and becomes a part of her family.
- Young Justice: Just as Artemis and Wally are reunited after her Reverse Mole mission with Kaldur, Wally dies saving the Earth. Artemis then takes on the Tigress name full time in order to cope with his death.
- In Steven Universe, Pearl is still mourning Rose Quartz, which is a large part of her character arc and the driving force behind several of her more "iffy" actions.
- Finn from Adventure Time succumbs to this first after he is rejected by Princess Bubblegum, and then to a greater extent when Flame Princess dumps him. In both cases, he falls hard and takes quite a while to cheer up again.
- Vinnie becomes this in the 2006 revival of Biker Mice from Mars. In "Turf Wars", he finds out that his old girlfriend Harley is still alive, only to find out that she has sided with the Nomad Rats because she was horribly scarred during the Plutarkian invasion and believed that the Biker Mice abandoned her. To make things worse, after Harley finally comes to her senses, she supposedly dies after taking it upon herself to stop the regenerator from going critical and causing Olympus Mons to erupt.
- Supposedly T.E. Lawrence aka "Lawrence of Arabia" aka "Emir Dynamite" loved Janet Laurie who rejected him.
- Theodore Roosevelt was heartbroken over the death of his son in World War I. The sheer will that kept him in good health quickly faded. Death by Despair soon followed.
- And decades before that, his first wife died on the same day as his mother did. His late wife's use of "Teddy" as an Affectionate Nickname for him is why he hated hearing it from anyone else.
- An iconic picture taken after the Our Lady of the Angels School Fire shows tough and rugged firefighter Richard Scheidt openly weeping while holding the body of John Jajkowski in his arms◊. This image is credited as the poster image of major fire-safety reform.
- In 2012, a picture was taken at the scene of a fatal car accident, where a cop had broken down, and was praying in tears on the side of the road. The victims had been seven and nine years old.
- Julie d'Aubigny was a famed opera singer, duelist, and all-around troublemaker in 17th century France, who was notorious for leaving a trail of broken hearts wherever she went. However, when her last lover, Marie Louise Thérèse, died, Julie was so profoundly heartbroken that she retired from the opera and from public life, and spent the rest of her short life in a convent.