27 Breakups That Broke Our Hearts

We knew it was coming. These high school sweethearts made us squeal happily in the first few seasons of the CW hit. However, after Elena became a vampire, her attraction to Damon was undeniable and their chemistry was top notch. It didn’t make it any less heartbreaking when Stefan stepped aside to let Elena follow her heart. While many of us still hold out for the two to reunite before The Vampire Diaries ends for good, it seems highly unlikely.

Angel did the noble thing in leaving Sunnydale in order for Buffy to move on, but why, oh why, did it have to happen like this? Their final dance together at the prom was Buffy’s happiest and saddest moment and left us all cursing Angel’s spinoff series, Angel.

When Kate told her husband Rick that she needed to get in her right head, and figure things out before they could live happily ever after, we’re not sure who was more stunned. Was it Rick, the actual man being spoken to, or was it fans of the long running series who finally believed that the will-they-won’t-they couple were going to be happy forever? This breakup left us just as gobsmacked as Rick.

This was the breakup we all saw coming, but hoped it changed directions. Luke and Lorelai had a rough time communicating before the revelation of his daughter, April, but after? It became a real chore for Stars Hollow’s power couple. Lorelai’s ultimatum to Luke didn’t end the way she, nor the audience (oh, the Christopher timeline…), had hoped it would.

We know that Jane needed to take a break from guys to focus on the one who most mattered, her son Mateo. But to watch Jane’s heartbreak after finally realizing what Michael meant to her, only to have it ripped away, killed us. Can’t these two just make it stick?!

What would life be like for the Winchesters if they walked away from hunting? We got to find out in season six when Dean stopped hunting and shacked up with old girlfriend Lisa and her young son. Dean became a family man, a surrogate dad, and unafraid of the things that went bump in the night. But the danger to Lisa became all too real when the supernatural found Dean again, and so Dean asked Castiel to remove all of hers and Ben’s memories of him. Dean, you almost had it all. We know, it hurt.

The image of Christina, a pile of emotion on the floor after being left at the altar by Burke, is burned into our memories. Even more gut wrenching? The moment she shouts that she can’t breathe, and Meredith cuts her out of her wedding dress. If you didn’t cry, you’re a robot.

This might be one of the harder pills to swallow if you were a fan of the couple. Rose never even got to hear the Doctor finish telling her that he loved her before they were ripped away from each other forever in the time vortex. Are you crying again just thinking about it? Sorry. We’ll grab you a tissue.

Remember when Chuck tried to set up Blair to sleep with his creeper uncle, and the greatest romance in Gossip Girl history was destroyed? Yeah, we do too, though we’d prefer to forget it. We know they got a happy ending eventually, but nothing will make us forget the look on Blair’s face when she realized what was actually happening.

We suppose the writing was on the wall. He wanted to postpone the wedding and then they delayed moving in together. But it doesn’t change the fact that the breakup of “Burzek” was an emotional gut punch that fans of Chicago P.D. weren’t ready for.

Sure, we all knew that Aidan was never going to be as exciting as Mr. Big. Butit was no e xcuse for Carrie to treat Aidan like crap. After accepting his marriage proposal, she refused to wear her engagement ring. When Aidan asked her why, she didn’t have a good answer, and he walked away from her, for good. This breakup didn’t leave us broken hearted for Carrie…our hearts ached for Aidan, the perfect guy that Carrie tossed aside.

Mindy and Danny’s first kiss on the airplane was some kind of sexy, and fans were excited to see that the two characters were finally going to connect. Fast forward just two episodes, to the moment when Danny ended his romance with Mindy before it could even begin.

This was a rough one for us. We spent an entire season leading up to Barney and Robin’s wedding, after reveling in their perfect love story, only to discover that the pair divorced shortly after in the series finale, leaving the door open for Robin to reunite with Ted. Barney and Robin seemed so well suited for one another and knowing they aren’t blissfully off playing laser tag and drinking scotch together is a crime that the HIMYM writers should go to jail for.

Callie and Arizona had been on the rocks for a long time, but we still held out hope that their relationship could be repaired through therapy, infidelity, trust issues, and family decisions. But sadly, there would be no happy reconciliation for these two, and Grey’s fans said goodbye to one of the series’ favorite couples.

Mark and Sarah were seemingly a match made in heaven. After failed romances out the wazoo, Sarah was able to settle in comfortably with Mark, despite many things that could have been roadblocks for the pair. But what Sarah couldn’t reconcile her feelings for Hank, and unfortunately, it would be the one thing that Sarah and Mark couldn’t handle together. We’re pretty sure that Mark bounced back, but when Sarah broke his heart, we felt it too.

There were no two people who deserved one another more than Don and Betty Draper. While we didn’t love Betty, and she was completely justified in leaving Don, her cheating husband, it still hurt to see these two crazy kids get divorced. Don had finally made himself emotionally vulnerable to a woman…unfortunately it was far too late.

Pacey never believed he was good enough for Joey, even though it was obvious to EVERYONE that he was. When he dumped her right before graduation, it drove us all crazy. Who would ever be more worthy of Joey Potter than Pacey? (Spoiler alert: No one, thank goodness.)

Rachel and Finn planned to get married after graduation. They were on the way to City Hall, in fact, when Finn took a detour to the train station in order to send Rachel off to New York City to follow her dreams of becoming a Broadway star. Their goodbye was noble, and Finn’s act selfless, but we hated it all the same.

We were so surprised at how much we loved Spencer and Toby’s romance. They were sweet, matched each other’s needs, and they were hot. Like, really hot. So we were all just as crushed as Spencer to discover that Toby was a member of the A Squad torturing Spencer and her friends. Her sad breakdown was ours, as well.

One of the sexiest couples on television, Alicia and Will, unfortunately, never got a happy ending because Will was shot and killed. Alicia’s heartbreak and grieving was ours, because we had such hope for these two. We still grieve with her now, especially after her recent discovery of his love confession voicemail way back from Season 1.

Zack and Kelly were Bayside High’s Barbie and Ken, the perfect couple. While Zack was completely devoted to Kelly, she got a little too close to her boss at The Max, Jeff, and ended up cheating on Preppy. It was the only time in the series that we really, really hated Kelly. When she asks Zack if they can still be friends, we all shouted, “NO!” as he quietly whispered, “Forever,” through tears.

Willow and Tara’s romance was perfect. The two witches were nothing short of magical. But when Willow started using too much magic, despite Tara’s asking her not to, friction began between the pair. It was too much for Tara when she discovered that Willow had erased a part of her memory in order to cover up a fight. Tara left Willow, wishing she could stay, but knowing that Willow needed help that she just couldn’t give her.

Isn’t this one obvious? We can debate whether or not they were really on a break during Ross’s discretion and whether or not Rachel was emotionally cheating with Mark, but one thing we all agree on? This first breakup between the tent pole couple was devastating.

We were all excited that Ben and Leslie had finally embraced their love for each other, granted it needed to be a secret so that they’d keep their jobs. However, a chance to run for City Council gave Leslie a lot to think about…expose her secret romance or follow her dreams? What’s a Pawnee girl to do? Ben decided for her, and broke up with her, handing her a “Knope 2012” button. It shattered us. Luckily, we had to endure a Leslie and Ben breakup for just six episodes before they reunited and it felt so good, but the breakup itself? Just awful.

Brenda Walsh and Dylan McKay were the essence of teen romance. He was a bad boy who was just so good. She was a good girl who was just bad enough. And when she went away to Paris for the summer, bad boy Dylan took up a romance with her best friend, Kelly Taylor. It’s one thing to break up with your boyfriend, but to lose your best friend as well, at the same time? Oh Brenda, we felt it too.

Everyone remembers his or her first breakup. Rory’s was particularly gut wrenching because Dean had just told her he loved her on their 3 month anniversary. When she didn’t immediately return his love, he freaked out and broke her heart. Say what you will about Team Jess and Team Logan, but when Rory said the line, “I’m ready to wallow now,” and broke down in tears, all we wanted was Team Dean and Rory back again.

Who knew that the couple we most wanted to see together would also be the couple who we would hate the most? Regardless of how you felt about the way that Jess and Nick changed the dynamic of the adorkable sitcom, there’s no arguing that their sudden breakup, while putting together a friend’s gift, broke your heart. The loft wouldn’t be the same again for a long time.