Top 10 Saddest Vampire Diaries Moments

The Top Ten
When Elena's Slumber Goodbyes (6x22)

Kai casts a spell linking Elena and Bonnie's lives, rendering Elena unconscious while Bonnie is alive.
In a series of visions or dreams, Elena and her friends and family say their goodbyes.

Elena is the best character on the show. I literally cannot stop crying every time I see this. How do you watch TVD without Elena?

When Stefan and Elena Broke Up for Real (2x06)

When Stefan and Elena broke up because of Katherine, it was so painful.

I loved them. They were goals and the best couple on TV. End of discussion.

I really voted for this one because the look on Stefan's face broke my heart.

When Aunt Jenna's Funeral Happened (2x21)

My eyes were bawling out, and I sobbed loudly. She didn't deserve this to happen to her, and this is shown by how her heart remained pure even when she died.
All the factors that led up to her death - her relationship with Elena and Jeremy, not to mention John's monologue and the music in the background - made this the saddest moment pre-season four, in my opinion.

Jenna was amazing. I hated Katherine when I saw that she selfishly allowed Jenna to die.
Yet Katherine gets all the credit. People sympathize with her. It is so unreasonable.

When Caroline's Dad Died (3x13)

Caroline's dad didn't want to be a vampire, so he chose to die instead.

When Alaric Died (3x20)

Everyone loved Alaric for what he did for Elena and Jeremy by taking them in. And when he died, the scene became even more painful when they all said their goodbyes.

This was the saddest thing ever. Their goodbyes made me cry.

I wish he hadn't died. He was Elena's last parental figure.

When Elena Died (3x22)

Stefan was the one who saved her and Matt. Elena sacrificed herself, and Stefan respected her choice. Then, she became a vampire.

When Damon Went to Alaric's Grave (4x02)

Damon and Ric's friendship is extraordinary. And when Ric died, I know that a part of Damon just died too.

No... This was so sad. And the whole time Damon was talking, Alaric was there listening.

The saddest moment EVER! I cried, and I don't cry in movies. When Damon was talking and Alaric was listening, Damon tried making jokes to hide his grief.

When Liz Forbes Died (6x14, "Stay")

Liz Forbes (Caroline's mom) dies of glioblastoma in this episode.

When Caroline was a child and asked her mom if she was going to die.

Liz's death has me bawling every time. It beats everything else for me.

When Stefan Died (8x16)

My heart. Most people don't regard Stefan in good taste, but I was overly attached to him from the beginning. He lost everything he had ever loved - his dad, his mom, his brother, Elena, Lexi, and even Katherine at one point. When he finally found happiness and a life with Caroline, he gave that up too.
His death reminds me of all the things he did when his switch wasn't flipped, all the things human Stefan did, and never once would I want him to change. He's perfect, even with his flaws.

Not only his death, but Caroline's phone call to him, and the fact that they had just gotten married, broke my heart.

When Damon ''Died'' (5x22)

Watching Elena box up her and Damon's things - man, it's heartbreaking. Plus, the song Salvation put the icing on the cake. I've never seen Elena break down so badly.

It's like a part of everyone died! It's a promise from seasons past (Season 3) broken! He died for his brother! Unbelievable!

This scene absolutely ruined me. Saddest moment ever!

The Newcomers

? When Bonnie Told Jeremy She Loved Him (5x22)
? When Damon and Caroline Were at Stefan's Grave and Saw Elena (8x16)
The Contenders
When Stefan Killed Enzo (8x11)

I literally sobbed when Stefan dropped Enzo's heart on the ground. The look on his face as he falls to the ground dead destroyed me! Bonnie's pained screams absolutely broke my heart.
Benzo was absolutely my favorite couple throughout the entire series, and I cried so hard when Enzo died.

Benzo was the best couple on the show - so pure with so much development. Bonnie and Enzo deserved better, and every time I watch this scene, I cry.

This was so sad I started to hate Stefan, but he was in his Ripper phase, so I couldn't blame him. I definitely cried.

When Damon Cried and Let Go of His Brother (8x16)

Damon doesn't seem to get emotional, so when he did, it was heartbreaking.

When Stefan Saw Lexi (4x22)

Their friendship is unlike any other. It's too bad she didn't get to stay long.

When Elena Switched Her Humanity (4x15)

It broke my heart when Jeremy died. Seeing Elena so sad made me cry so much. And when Elena burned down the house, it was probably the saddest thing ever.

When Jeremy died, Elena couldn't handle the pain, so she decided to switch off the pain by switching off her humanity.

Nina's acting was honestly incredible in this scene. I cry every time.

When Damon Let Elena Go (5x22)

Literally made me cry for hours. Such an emotional scene.

When Caroline Phoned Stefan (8x16)

This was one of the saddest moments in this episode for my friend and me. When Caroline phones Stefan and tells him how much she loves him and that she understands that he sacrificed himself for his brother, it was heartbreaking.
Currently crying while writing this.

When Enzo Died (8x11)
When Klaus Had to Give Up on Caroline (5x11, "500 Years of Solitude")

He never gave up on her. He just let her realize her wishes for life, and he decided to give her the choice to come to him when she was ready. He never gave up on her.

When Rose Died (2x12)

I cried every time I saw this scene.

Damon comforts Rose as she lies feverishly in bed. She remembers her old life on a sunny hillside with horses all around and dreams that Damon is there. He's controlling her dream. Rose says she misses being human and mattering to people. She thanks him for making the pain go away, saying she's not afraid anymore. In bed, he gently lets go of her hand.

On the sunny hillside, Rose challenges him to a race to the trees. As she counts to three, back in bed, he slowly takes out a stake and positions it over her heart. When she reaches three, he drives it in.

When Bonnie Died (5x04)

No matter how many times I watch this show, Bonnie's death always brings tears to my eyes.
I don't know, this whole show makes me so emotional, but Bonnie's death brings the waterworks.

When Stefan Was Reunited with Lexi in the Afterlife (8x16)
When Damon Confessed His Love for Elena but Had to Compel Her (2x08)

At first, I hated Damon, but as I kept watching the show, I began loving him so much. What really had my tears running down like a river was when both Katherine and Elena chose Stefan over Damon, even though he was always the one who loved them without getting it back. And when he confessed it to Elena, he had to compel her so she wouldn't remember him saying it. It was one of the saddest moments for me.

When Jeremy Died (4x14)
When Everyone Saw the Dead People They Missed (8x16)
When Nadia Petrova Died (5x15, "Gone Girl")
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