The 7 Worst TV Breakups Of All Time

Brit + Co's Picks For The Worst TV Breakups

Rory and Jess from Gilmore Girls

This is one of my personal worst TV breakups because it seems like, out of all of Rory's boyfriends, Rory and Jess are going to stay together forever when they start dating. Not only does their love of books bring them closer together, but their personalities are so compatible — they're perfect for each other, IMO! But when Jess leaves for California at the end of season 3 (without saying anything to Rory, I might add) is unacceptable! They see each other a few more times over the course of the show, but it's never the same. This ending breaks my heart, and based on the final look he gives Rory during A Year in the Life, he also regrets it BIG TIME.

Ross and Rachel from Friends

Friends is one of the most iconic sitcoms of all times, and Ross and Rachel is definitely one of the worst TV breakups. In season 3, this iconic couple decides to take a break, and in "The One with the Morning After," Ross wakes up with another woman named Chloe at the exact moment Rachel shows up at his door to get back together. Rachel finds out about the affair, and after a fight in Monica's living room, the couple calls it quits.

Regardless of how you feel about Ross using every opportunity to point out they "were on a break" when he slept with Chloe, seeing Rachel's reaction (and knowing the trust between them was broken) is one of the worst moments in the whole show. Just thinking about it makes my stomach bottom out!

Damon and Elena from The Vampire Diaries

This Vampire Diaries couple was truly endgame, and I can't lie: The will-they-won't-they of it all was one of my favorite things about the show. So when they broke up (to my horror), I was devastated.

Damon and Elena admit they're bad for each other in the season 5 episode "While You Were Sleeping" (then Damon tells her he doesn't even want to be friends. Ouch!!), but it's the season finale, "Home," that makes me extra emotional. When Damon gets stuck with Bonnie on the Other Side, he says goodbye to Elena, who's begging him not to leave but can neither see nor hear him. Say it with me: gut! wrenching!

Conrad and Belly from The Summer I Turned Pretty

The Summer I Turned Pretty fans are PASSIONATE about whether they're team Conrad or team Jeremiah (trick question, my OTP is Taylor and Stephen), and even the most dedicated Conrad stan hates the prom scene. You know, when he breaks up with Belly at her prom, in the rain. I know he just thinks Belly deserves better, but it's still very painful to watch. (Not quite as painful as him realizing Belly didn't know he loved her in episode 6).

Fleabag and The Priest on Fleabag

In the history of TV, I don't think I've ever heard anything as heartbreaking as "I love you," "It'll pass." Like, who approved that line?! The viral moment comes at the end of the Fleabag series finale, when Fleabag is sitting with The Priest at the bus stop. Over the course of the series, we not only see how much these two care about each other, but how well they know each other (like how The Priest recognizes when Fleabag zones out). To be loved is to be known, and that's what makes this devastating TV breakup even more devastating.

Schmidt and Cece from New Girl

When I hear "worst TV breakup" I IMMEDIATELY think of Schmidt and Cece from New Girl. Schmidt gets away with a lot of ridiculous things throughout this show, but dating two girls at one time is not one of them (nor should it be). After Nick has a hard time keeping Schmidt's love life secret, Schmidt finally comes clean to Cece in "Double Date," leaving both her and me in tears. No matter how many times you rewatch the show, it truly feels like their relationship (and maybe even the friend group) will never recover.

Carrie and Aidan on Sex and the City

After so much back and forth, it's hard to accept Carrie and Aidan's final breakup on SATC. But in season 4's "Change of a Dress," Carrie realizes she's not ready for marriage and Aidan realizes he doesn't trust her after her affair with Big. The combo of broken trust and being at two different life stages makes this extra painful to watch, and I don't think any amount of rewatches (or And Just Like That binges) is going to change that.