Almost everyone on The Vampire Diaries has had a death scene it’s like TVD’s rite of passage. But not all television character deaths are created equal, and while some TVD demises have left us shrugging our shoulders, others have left us sobbing on the floor. With the looming potential death of Katherine Pierce in the 100th episode, we take a look back at the saddest character deaths in TVD history.

Lexi Branson

We lost Lexi before we really even had a chance to get to know her but that doesn’t mean her death didn’t sting oh-so-bad given the circumstances of her demise: Lexi came to town for Stefan’s birthday in Season 1, and you could quickly tell how close these two vampires besties were. Unfortunately for all involved, Damon was still in Homicidal Phase at this point. He staked Lexi. Right in front of Stefan. On his birthday. This death only gets sadder the more we learn through flashbacks about Stefan’s loyal best friend.

Rose

Rose’s death hit us pretty hard not because we necessarily had a strong emotional connection to her character though she seemed pretty cool but because Damon did. Though we totally already knew Damon was a marshmallow on the inside, his short relationship with Rose in Season 2 gave us added insight into just how sensitive this vamp could be. Eventually, it was Damon who killed Rose to save her the slow, painful death a vampire undergoes when bitten by a werewolf and it was so hard to watch.

Aunt Jenna

Oh man, Aunt Jenna’s death was the worst. Not only had this character been with us since the pilot, but she was the third parental figure Jeremy and Elena lost in the span of a few years. Not to mention that her murder at Klaus’ hands happened right after she had reconciled with boyfriend, Alaric who also lost his first wife to supernatural shenanigans (though, admittedly, of a different variety). R.I.P., Aunt Jenna. We can’t wait to see you again in the 100th episode.

Carol Lockwood

Credit: The CW

Like Aunt Jenna, Carol Lockwood was both murdered by Klaus and left someone (i.e. Tyler) behind as an orphan with her untimely demise. (Maybe this list wasn’t such a good idea. It’s only reminding us how many parental figures Klaus has killed.) We were sad to see Carol go in such a senseless way not only was she Tyler’s only family, but she was a total ally to the TVDers. Now, Sheriff Forbes has to deal with town politics all on her lonesome.

Alaric Saltzman

Alaric died a lot on this show (thank you, Gilbert ring) and it hurt each and every time. His final few deaths, though, may have involved some ugly crying on our part. Alaric was an integral member of the group: a parental figure for Jeremy and Elena, a bestie for Damon, and an all-around great guy. His final death came about when Elena drowned, as his life force had been linked to hers by Original witch, Esther. However sporadically evil his long, slow demise was, we bet you cried at the beautiful memorial service the Mystic Falls gang held for him. (Don’t lie. We know you did.)

Elena Gilbert

Perhaps no death was more jarring to the show than the one of its central protagonist. At the end of Season 3, the car Elena and Matt are driving is forced off a bridge and into the water. Elena convinces Stefan to save Matt first, and ends up dying as a result. The fact that she quickly came back as a vamp didn’t make this particular death any less affecting. Watching Elena mourn her human self for most of Season 4 was like the death that kept on giving (pain).

Jeremy Gilbert

Jeremy’s death, another that was eventually reversed, was a real emotional low point for this show. Like, seriously. If you didn’t bawl while watching Elena-in-denial first guard Jeremy’s rotting body, then burn down her childhood home (Jeremy’s corpse inside) when she’s accepted the truth, then you probably don’t have lacrimal glands. We still get teary-eyed thinking about the post-Jeremy’s death string of episodes.

Which TVD death has hit you the hardest? Will you be terribly distraught if Katherine dies? Sound off in the comments below!

Catch the next episode of The Vampire Diaries on Thursday, January 23, 2014 at 8 p.m. ET on the CW, followed by an all-new episode of Reign.

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