27 Breakups That Broke Our Hearts

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.