Although Lexi died in the first The Vampire Diaries episode she appeared in, her impact in those short 40 minutes was felt throughout all eight seasons. Whenever Lexi returned (via ghost form, of course), it was a celebration, and her and Stefan's reunion was one of the best parts of the series finale. So looking back on when Damon drove a stake through Lexi's heart in The Vampire Diaries season 1, episode 8 hurts a lot more than watching it when it first aired.
Jenna's death in The Vampire Diaries season 2, episode 21, was arguably the CW series' first major death, and it was a sad occasion, to say the least. Klaus, one of the more controversial characters in The Vampire Diaries universe, was Aunt Jenna's murderer (after he turned her into a vampire). And after this episode, Elena lost yet another parental figure. Her death was a turning point in the series, and no one could forget the heartbreaking moment Elena told Jenna to turn her humanity off so that she wouldn't be scared when Klaus inevitably killed her.
Nina Dobrev is undoubtedly one of the best criers in Hollywood, and she put her talents to good use as Elena in The Vampire Diaries. But her best work came in season 4 when Jeremy died, and Elena was completely and utterly heartbroken. As sobs wracked her body, Elena begged to make the hurt stop, so Damon instructed her to turn her humanity off so that it could all go away. Of course, that would go on to be a terrible decision, which made the scene all the more tragic.
Following Bonnie's death at the end of The Vampire Diaries season 4, Elena, Damon, Caroline, Matt, and Jeremy held a funeral for her in the fourth episode of season 5 (when Jeremy finally told them she died). Thankfully, Bonnie would be resurrected later on, but seeing the people she loved the most say their goodbyes to her is still painful to this day. They each left Bonnie something on a tree stump in the forest, and it was a hauntingly beautiful scene that would make a tear come to anyone's eye.
It seems as though the saddest The Vampire Diaries scenes have one thing in common — death. During the season 5 finale, Damon and Bonnie got trapped on the Other Side, meaning they had to say their goodbyes to their loved ones; for Damon, that was Elena. Unfortunately, she couldn't see him since he was on another plane, but Damon could see her, and Elena knew he was there. She begged him not to leave her, and Damon replied, "I don't have a choice, baby." Once again, Nina Dobrev turned on the tears, and her acting combined with Damon's words was enough to leave viewers in shambles.
Elena was not the only one torn apart by Damon's absence following The Vampire Diaries season 5 finale — Stefan was also a wreck. He admitted as much during the final scene of season 6, episode 5, when he went to the Salvatore crypt to air out his feelings. Stefan spoke to his brother and said, "I'm not doing so great without you ... Because I'm lost, brother. I'm lost." Frustrated, Stefan threw a bourbon bottle across the room just for Damon, who had returned from the Other Side, to catch it. The two brothers, who had been through so much throughout The Vampire Diaries, embraced, and it seemed like nothing else mattered.
Sheriff Liz Forbes was a part of two of the best dynamics in The Vampire Diaries —the mother/daughter relationship between her and Caroline and her friendship with Damon. So when Liz died, not due to some supernatural cause, but because of a very real and horrific disease, in the middle of season 6, the audience grieved alongside the characters. Liz's death scene was heartbreaking, of course. But it didn't hold a candle to her funeral, which featured Caroline singing, Damon giving a eulogy, and police officers draping the American flag over Liz's casket.
Following her mother's death, Caroline turned her humanity off in The Vampire Diaries season 6, which led to her carelessly burning the last letter Liz left for her. But when Stefan showed Caroline a memory of him with Liz, her humanity returned, and she was full of regret. Sadly, Caroline never found out what Liz wrote in the letter, which was a tough pill to swallow, despite the countless cherished memories she had of her mom.
Enzo wasn't the most beloved character when he was introduced in The Vampire Diaries season 5, and his sudden romance with Bonnie was unexpected. But Enzo and his relationship with Bonnie grew on some viewers. Unfortunately, just as the audience was falling in love with Enzo and Bonnie's love, Stefan ripped Enzo's heart out right in front of Bonnie. After giving Stefan the cure, Bonnie raced to Enzo and held his dead body in her arms as she let out a piercing cry that, as viewers found out later, literally opened the door between hell and earth.
In the episodes leading up to the series finale of The Vampire Diaries, some fans were worried that one of the Salvatore brothers would die, and unfortunately, their fears came true. Damon was determined to be the one to make the sacrifice to ensure Katherine went to hell when Bonnie sent the hellfire back to its home. He even compelled Stefan, who had been turned into a human, to let him be the martyr. However, Stefan took vervain. So he gave Damon the cure and pushed him out of the way so that he could make the sacrifice instead of Damon.