If The Vampire Diaries has heart-breaking down to an art form, then Damon Salvatore (Ian Somerhalder) is one of its most effective tools. No one can make that broody, heartbroken face quite like Damon (maybe because he’s seen it on the faces of the many people whose hearts he literally has ripped from their chests). Whatever his secret, here’s a roundup of Damon’s most heartbreaking scenes. Hope you brought a tissue!

Stefan makes Damon complete the transition (Season 1, Episode 20)

One of the best and most heartbreaking episodes of all time was the story of how Damon and Stefan became vampires in Season 1’s “Blood Brothers.” When Elena mistakenly believes that Damon has been punishing Stefan for the last century-and-a-half for letting Katherine allegedly die, Damon tells her the truth: he has been punishing him for making him complete the transformation into vampirism. The Civil War-era flashbacks show us that Damon wanted to die, but Stefan coaxed him into feeding. The revelation that Damon never wanted to be the immortal monster he eventually became doesn’t justify any of his actions, but it does make them that much more tragic.

He tells Elena he loves her, then makes her forget (Season 2, Episode 9)

In Season 2, TVD was still firmly in Stelena mode, but apparently, no one gave Damon the memo. He confesses his love to Elena one night in her bedroom, telling her that “Because I love you ... I can’t be selfish with you.” Then, he compels her to forget. It’s so sad, but also kind of awesome because, when Elena turns vamp two seasons later, she totally remembers it. Well played, TVD. Well played.

Rose dies in his arms (Season 2, Episode 12)

Talk about a tear-jerker! When Rose takes a werewolf bite meant for Damon, the seemingly cold-hearted vamp holds Rose as she dies from the venom. He imagines them into a wonderful dream together and, when she’s at her happiest, he mercy-kills her. For a relationship that lasted not-so-long, this was a serious heartbreaker.

Katherine tells him she never loved him (Season 2, Episode 1)

At this heart, Damon is a consummate romantic. Which is what makes his unrequited love for Katherine so damn sad. Damon has loved and missed Katherine for 145 years, thinking she was lost to him in a Mystic Falls tomb he couldn’t enter. When the tomb is finally opened, however, it turns out Katherine was never in it. She’s been gallivanting around the world without Damon all this time. In the Season 2 premiere, Damon offers to forget everything that has happened so they can start over. He loves her that damn much. She tells him: “The truth is I’ve never loved you. It was always Stefan.” Harsh.

He breaks up with Elena (Season 5, Episode 10)

It’s been a tough few episodes for Delena, and it all started when Damon decided he needed to break up with Elena to keep from tainting her goodness with his evilness. Or something like that. Watching him yell, “Stop defending me!” at Elena was really tough to watch. Especially now that we know what came next in their star-crossed romance.

“Elena” breaks up with him (Season 5, Episode 12)

You may have guessed that it was this scene in last week’s episode that prompted this list. Watching Elena run into Damon’s arms, only to have Katherine take over her body mid-embrace was just bad enough. Then, we had to watch Damon give his heart to Elena, only to have “Elena” (read: Katherine) thoroughly stomp on it. The angst!

Which Damon scene do you think is the most heartbreaking? Sound off in the comments below!

The Vampire Diaries airs Thursday nights at 8 p.m. ET on The CW.

Kayti Burt is a contributing writer for Wetpaint Entertainment with a penchant for all things pop culture. Follow her on Twitter and Google+!