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- Dexter's flashback to what happened to him as a child, when he is faced with a crime scene that triggers the repressed memory of seeing his mother being murdered with a chainsaw in front of him when he was three, and being left in a shipping container with her body and covered in her blood for days. The look on his face when he is overwhelmed by the full realization of what happened is heartbreaking. No wonder he's so messed up.
- At the end of Season 1, when Dexter is weeping in the corner after slitting his brother's throat, waiting for him to die. He says so himself that he was the first victim he truly regrets having to kill.
- What makes it worse is that Dexter killed the only person capable of accepting and understanding him for who he really is, his long lost brother who spent all those years just to find him.
- Debra trying to pretend she's fine in the back of the ambulance with Dexter, then completely breaking down and crying her eyes out, saying how scared she was and how grateful she is for Dexter saving her.
- From the end of Season 1, when Dexter imagines a parade in his honor, with people cheering him for keeping Miami safe and "protecting their children". Some find it funny, but when you think about Dexter saying this must be what it's like to walk in the light, it just shows you how lonely and unaccepted he feels and how he wishes he could get people's approval.
- Dexter's flashback to when Harry rescues him from the container, with his brother Brian calling out to Dexter, begging him to not leave him.
- Dexter's Imagine Spot in Season 2, in which he imagines himself as the superhero called the Dark Defender, saving his mother, his brother, and himself.
- Dexter meeting the man who was responsible for killing his mother. He has a huge freak out when he's about to kill him and just manages to stop before he does it, thanks to Lila. It's one of the rare moments where Dexter has a major breakdown.
- The flashback to Deb's birthday where Harry has a work-related outburst. She couldn't even get a break on that.
- Doakes' response to Dexter executing a serial killer right in front of him. You could tell that despite Dexter being the Bay Harbor Butcher, Doakes was actually trying to reason with him and talk sense into him - until that. Doakes' Heroic B.S.O.D., while short, is painful to watch.
- In that same episode, Dexter finds out that Harry actually died by committing suicide. It was caused by him walking in on Dexter killing a man and being so horrified at what he'd created that he couldn't live with himself. Dexter's own guilt for causing this is the icing on the cake.
- Dexter's final conversation with Doakes. It looks like the he's truly about to accept giving himself up and Doakes seems genuinely concerned at him. Sadly things change...
- LaGuerta crying after finding out Doakes has died, while trying to cover her tears by acting busy.
- The euthanasia scene in season 3. "You finally brought me the perfect pie."
- Especially so when their final words to each other are Dexter finally admitting he killed Brian, and Camilla reassures him it was the right thing to do.
- Deb going back to the parking lot where Lundy was killed. Whatever you might think about her, seeing her break down like that is truly heartbreaking.
- The end of Season 4, Dexter kills the Trinity Killer and comes home to find Rita dead in her bathtub, the entire bathroom covered in her blood with their infant son Harrison crying whilst sitting in the blood, echoing his own trauma. Dexter instantly grabs Harrison and runs outside, and the expression of grief on his face hits hard .
- When Dexter says "I hope you don't mind I picked out that dress you were wearing when we first met" to Rita's corpse in her coffin before the funeral. The way the line is delivered in a rushed, mumbled, and completely shell-shocked voice is just heartbreaking.
- Almost the entirety of the first episode of Season 5; Dexter breaks down after killing that guy with the boat anchor, Astor loses it after Dexter tells her of Rita's death, and Dexter realizes just how much he misses Rita and turns up to her funeral—shell-shocked and late—to give a heartbreaking speech about how much she meant to him.
- In the second episode, when Dexter sends the kids to live with their grandparents. His goodbye is heartbreaking, and the response from a still-furious Astor and a crying Cody is gut-wrenching.
- When Lumen says goodbye to Dexter in Season 5. One of the few times beyond his brother's death in Season 1 that Dexter has nearly teared up.
- Brother Sam's death. Considering he was truly trying to help Dexter and the fact that he was killed by Nick the former criminal he was trying to reform makes it all the more heartbreaking.
- Dexter being discovered by Deb could be seen this way. Considering it makes their bond go sour and ultimately break Deb's psyche.
- The death of Isaak.
- At the end of the season finale, not La Guerta's death, but Deb's reaction to it. Dexter walks over to her in an attempt to console her, only for Deb to spit out between choking sobs, "I hate you."
- Evelyn realizing her son must die, and later her death by his hands.
- It's hard not to cry after Debra died. Sure, it was a Mercy Kill on Dexter's behalf, and it was the least painful way to end her suffering after being pronounced brain dead, but still.
- Just the thought of Dexter having to murder his own sister is a tearjerker in its own right.
- Dexter saying "I love you Deb" just before the EKG flatlines is the perfect storm of feels.
- Imagine if you were one of the people who thought Dexter had died at sea after seeing the remnants of his boat.
- Dexter's ultimate fate as an Empty Shell.