* Knowing what happens to David Clarke makes watching Emily and Victoria's flashbacks fairly wrenching.
* The entire Premise of the series about how a sweet and optimistic young girl would be [[BreakTheCutie so beaten down by life and so many horrible people]] to become a cold and calculating near sociopath is upsetting.
* Emily and Nolan's fight in episode 10.
* The death of [[spoiler:Sammy]].
** Made all the worse by Jack's explanation that [[spoiler: Sammy is not just his best friend - he's also the last connection he has to Amanda.]]
* The fact that the first episode shows that by the time she got out of juvie, Amanda actually did believe that her father was a murderer.
* Emily thinks she's wrapped up the Revenge business and makes an excuse to go to Jack's place, presumably to confess to him. Then she sees that fake Amanda has returned, and is now pregnant.
* [[spoiler:Fake Amanda]] dying in Emily's arms after the boat explosion. The music, cinematography, flashback, significance of the necklace and Emily's sobbing all contribute to making this likely the most heartwrenching moment of the series. [[spoiler: Jack's]] grief is no less painful to watch.
** [[spoiler: Emily having to let go of Amanda's body as the life raft sinks.]]
--> [[spoiler:Amanda: Jack and my baby - I need you to take care of them...You've given me the one thing I thought I'd never have - a real family...]]
* [[spoiler: Padma's death at the hands of the Initiative, and Nolan's subsequent HeroicBSOD]] is heartwrenching. Just something in the way he cries in Emily's arms.
** It gets worse. [[spoiler: In the finale, we're treated to a video of Padma announcing Nolan as the mastermind behind everything. And all he can do is cry.]]
* [[spoiler: The entirety of Declan's last few scenes in the series. Declan doesn't know how bad his condition is when Jack tells him that he's planning on taking Carl and Declan somewhere far away from the Graysons and so he doesn't really object to Jack's plan save for mentioning that Charlotte's pregnant. It's clear once the doctor leaves the room that Dec knows something's wrong, but he lies to Charlotte for her sake, because he wants her last memory of him to be of him smiling rather than informing her of his condition. Declan's last conversation with Nolan involves telling Nolan to take care of Jack if something goes wrong. We're offered a bit of a HopeSpot when Nolan offers to bring in the best doctors, but Declan can only smile and tell Nolan what he needs is time, not money. Declan then dies off screen when his aortic artery ruptures, and Nolan is the one left to inform Jack.]]
** [[spoiler: Declan's final message to Jack. We're now left with the realization that Conrad's actions have led Jack losing almost everyone he's ever cared for, save for his son. And this is probably the nicest character in the show.]]
* Ashley's [[HumiliationConga Humiliation and]] TraumaCongaLine of being blackmailed into prostitution by Victoria and then mercilessly rejected by Daniel after he finds out
* [[spoiler: When Emily discovers that she will not be able have a baby due to the extent of her gunshot wounds]]
* In the Season 3 finale, Victoria [[spoiler: kills Aiden. And leaves his body in Emily's beach house as if he's still alive for her to find.]]
* Nolan getting [[spoiler: shamed by David Clarke on live TV because David mistakenly thinks Nolan stole Amanda's inheritance. It's well established that Nolan respects the living daylights out of David, and seeing him tear up is just brutal. Even worse, he obviously wants to say that he did give her the inheritance he can prove it, but even now he still protects Emily, because revealing her on TV would be against Emily's plan and potentially catastrophic.]]
* The Season 4 Winter finale Atonement [[spoiler:Daniel takes a fatal shot in the abdomen shielding Emily from Kate. While Jack shows up in time to take down Kate, Daniel dies in Emily's arms after she admits [[ItMeantSomethingToMe that despite all of her deceptions, she did love him]]]]
-->[[spoiler:Emily: I want you to know it wasn't all a lie, not with you]]
-->[[spoiler:Daniel: I know, I know...]]
** It get's worst [[spoiler: as Margaux had just recently revealed to Daniel that she was ready to forgive him and allow him back in her life and, here's the part where your heart hits the floor, their unborn child's as well]]
*** Believe it or not, it get's even worst, [[spoiler:the next episode ''Epitaph'' revolves around tarnishing his name, by letting the world believe that Emily shot Daniel in self defense from his drunken assault, under David claims that they must erase Kate's involvement to protect Emily, David, Victoria, Jack, Grayson, Charlotte, Margaux and so on from the [[FateWorseThanDeath wrath of Malcom should he discover his daughters death]]. Something that doesn't even sit well with Emily]]