The Vampire Diaries has had more than its fair share of character deaths. Not all of them have stuck, but that doesn’t mean they haven’t all provoked some intense feels from us fans. With Katherine’s death favored to go down in this Thursday’s 100th episode, we take a look back at the toughest characters deaths to come before. Which death was the saddest? You tell us!

Lexi Branson

Oh, Lexi, we hardly knew thee before you were unceremoniously staked by Damon in front of Stefan’s very eyes. Happy birthday, brother! Since Lexi’s Season 1 staking, we have only come to love Stefan’s loyal BFF more through flashbacks and ghostly appearances, making her death that much harder to stomach — and it was pretty hard to stomach to begin with.

Vicki Donovan

Credit: Quantrell Colbert/The CW ©2009 The CW Network

Vicki was the first series regular to bite it, and it was tough to handle, especially given how it went down. Turned by Damon, Vicki was unable to control her lust for blood. Stefan was forced to stake her to save her from killing Elena and Matt with her insatiable desire to feed. Vicki’s death devastated Matt, Jeremy, and Tyler — and added level of devastation to the loss of this charismatic character.

Anna

Credit: Bob Mahoney/The CW

Anna’s death was the second in a long string of Jeremy’s girlfriends who have died, but that didn’t make it any less painful. In the Season 1 finale, The Founder’s Council implemented their master plan to rid the town of vampires, literally pulling Anna from Jeremy’s arms to bring her to the church to kill her. We watched Damon watch her die at the hands of John Gilbert, and it was really sad.

Rose

Julie Plec recently called the scene in which Damon put Rose out her misery by killing her, than freaked out and killed an innocent girl as one of her all-time favorites in TVD history — and we can understand why. Watching Damon grieve Rose’s passing go from bravely sentimental to cowardly homicidal may have given us some serious narrative whiplash, but we’ll never forget the quiet, bittersweet moment when Damon let Rose go.

Aunt Jenna

We never expected the show to kill off Aunt Jenna, and that may have been part of the reason why this one stung so bad. Not to mention this was the last remaining family member Elena and Jeremy had after their parents died only a year before. Jenna was sacrificed by Klaus to complete a spell, which meant — unlike many of the characters on this list — she never really got a chance to say goodbye.

Carol Lockwood

Credit: The CW

Speaking of deaths committed at Klaus’ hand, Carol Lockwood was another on the list of Klaus’s inopportune murders. The Original hybrid killed Tyler’s mom in retribution for Tyler’s betrayal. This was super sad because not only was Mayor Lockwood a pretty cool lady, but she was also the second of Tyler’s parentals to die during the course of the series. Bummer.

Alaric Saltzman

Credit: The CW

It’s hard to talk about Alaric’s death — not only because his departure was so damn sad, but because he died quite a few times before his eventual permanent demise when Elena drowned in the Season 3 finale, so killing his life force. There is perhaps no TVD scene that has made us feel as much as the one in which Alaric chooses not to complete the transition to vampire and locks himself in a tomb to die. The cast gathers with candles in their formal wear to say goodbye, but — instead of speaking — they all relay their sadness in a shared look with their teacher and friend.

Elena Gilbert

There is perhaps no death that was more impactful to TVD than Elena’s in the Season 3 finale. After three seasons of trying so hard to stay alive, she finally dies and turns vampire — and it happens because she chooses to have Stefan save Matt over herself, and Stefan actually listens. Elena may have turned vamp, but a part of her died that night on the bridge, and the show is still mourning that girl.

Jeremy Gilbert

Don’t even get us started on Jeremy’s seemingly permanent death in Season 4. Katherine turned Elena’s baby brother over to Silas to nab The Cure for herself, and watching his loved ones try to deal — or, in Elena’s case, not deal — with his death was one of the most painful storylines TVD has ever given us. Sure, he came back in the end, but that didn’t lessen the turmoil we went through watching the gang deal with his death. (We’re not sure which scene made us cry more: Elena burning down her house with Jeremy’s body in it or Matt crying by himself in his truck. The misery!)

Bonnie Bennett

But, of course, Bonnie isn’t one to sit around and let her loved ones stay dead — so she traded her life for Jeremy’s, and that realization was pretty epic. Bonnie’s death was so difficult because it took so long for her loved ones to fully realize it, which in turn, let Bonnie pretend for so long that everything was OK. The memorial service the gang held in the woods once they did discover the truth about Bonnie’s death was unexpectedly gut-wrenching, given that Bonnie was technically there in ghost form.

Which death do you think was the saddest? Vote in our poll and 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+!