The Saddest TV Breakups of All Time

1 | Cristina/Burke, Grey’s Anatomy

It's not so much that we felt like Cristina (Sandra Oh) and Burke (Isaiah Washington) were meant to be together, but that the image of her breaking down in her wedding dress after being left at the altar has haunted us for years. She deserved so much better.

2 | Sam/Diane, Cheers

The tough thing about endgame couples like Sam (Ted Danson) and Diane (Shelley Long)—the pairing Cheers had been setting up from the beginning—is that sometimes the show goes on longer than one of the actors wants to be on it. Long decided to depart at the end of Season 5, forcing a bittersweet conclusion to this long-awaited romance. (Diane returned for the finale, but that didn't end well either.)

3 | Ross/Rachel, Friends

Whether or not you think they were on a break, and even if you know they eventually end up together (she got off the plane!), Ross and Rachel's breakup is arguably the most devastating Friends moment. They're each other's lobsters! Beyond that, Jennifer Aniston and David Schwimmer showcase the real emotional interiority of these sitcom characters.

4 | Carrie/Aidan, Sex and the City

Carrie (Sarah Jessica Parker) had a lot of not-so-great relationships over the course of Sex and the City, but if we had to pick one man who actually seemed to treat her right, it would clearly be Aidan (John Corbett). Unfortunately, she wasn't ready for commitment. (The less said about his appearance in the awful second movie, the better.)

5 | Rory/Dean, Gilmore Girls

While many people took Rory's (Alexis Bledel) breakup with Jess (Milo Ventimiglia) harder than her split from Dean (Jared Padalecki)—her telling him she was in love with him over the phone before ending things certainly stung—there's nothing like the heartbreak of losing your first love.

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6 | Santana/Brittany, Glee

Glee didn't always use pop songs to its advantage, sometimes choosing a recent hit simply because it was getting a lot of radio play. In the case of Santana (Naya Rivera) and Brittany's (Heather Morris) breakup, however, the show had the late Rivera deliver a pitch-perfect performance of Taylor Swift's "Mine" that completely wrecked us.

7 | Pacey/Joey, Dawson’s Creek

Most Dawson's Creek fans agree that Joey (Katie Holmes) and Pacey (Joshua Jackson) always made more sense together than Joey and Dawson (James Van Der Beek) did. Thankfully, the show also realized that, solidifying their romance for good in the series finale. But there were bumps along the road, including a particularly brutal breakup at the prom.

8 | Sheldon/Amy, The Big Bang Theory

After struggling to articulate and act on his feelings for Amy (Mayim Bialik), Sheldon (Jim Parsons) finally decides to propose to her—but she breaks up with him before he can go through with it. For a series that didn't often make us emotional, this gut-punch of a season finale got us good.

9 | Jess/Nick, New Girl

This is another one of those will-they-or-won't-they TV pairings where they will and they do... and then they don't. Of course, Jess (Zooey Deschanel) and Nick (Jake Johnson) do find their way to each other again, but it's still hard seeing them split up when they realize they're in different places in life.

10 | Brenda/Dylan, Beverly Hills, 90210

True Beverly Hills, 90210 fans will never be able to hear R.E.M.'s "Losing My Religion" without remembering Dylan (Luke Perry) and Brenda's (Shannen Doherty) breakup after a pregnancy scare. This wasn't even their worst breakup, but it was a painful reminder that even the coolest '90s couple couldn't last forever.

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11 | Lily/Marshall, How I Met Your Mother

Lily (Alyson Hannigan) and Marshall (Jason Segel) seemed like the stable couple on How I Met Your Mother, and they were for most of the show's run. That didn't stop them from breaking up at the end of the first season, leaving Marshall to wallow in his grief during their summer apart, and forcing viewers to do the same.

12 | Willow/Tara, Buffy the Vampire Slayer

What is it about Alyson Hannigan and TV breakups? Years before How I Met Your Mother, she showcased her tremendous crying skills when Tara (Amber Benson) left Willow over Willow's magic manipulation. The use of Michelle Branch's "Goodbye to You" makes this the most memorable Buffy the Vampire Slayer breakup. And the fact that Tara dies right after they get back together adds another layer of pain.

13 | Eric/Donna, That ‘70s Show

With some exceptions, high school couples aren't really meant to last forever. TV shows often have them get back together in the end—as That '70s Show did when Topher Grace returned for the series finale—but we still grieved Eric and Donna (Laura Prepon) realizing they had to part ways.

14 | Alexis/Ted, Schitt’s Creek

Sometimes the mature breakups are the hardest to endure. Alexis (Annie Murphy) and Ted (Dustin Milligan) are very much still in love with each other when they decide to split up, and that makes it all the more upsetting. Their final romantic meal together is almost unbearably bittersweet.

15 | Kevin/Winnie, The Wonder Years

Kevin (Fred Savage) and Winnie (Danica McKellar) got together and broke up repeatedly throughout The Wonder Years, but the moment that hurt the most was Winnie telling Kevin she'd met someone else. That is, until the series finale revealed that Kevin went on to marry and have a family with someone else.

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16 | Olivia/Fitz, Scandal

In many ways, Olivia (Kerry Washington) and Fitz's (Tony Goldwyn) relationship had overstayed its welcome on Scandal by the time these two finally ended their affair for good. That doesn't mean we didn't cry when it actually happened. So much for that house in Vermont.

17 | Veronica/Logan, Veronica Mars

Don't worry—while Logan (Jason Dohring) broke up with Veronica (Kristen Bell), the couple known online as LoVe found their way to each other again, even getting married in the revival season. Just do yourself a favor and don't read about what happens to Logan immediately after that.

18 | Blair/Chuck, Gossip Girl

Blair (Leighton Meester) and Chuck (Ed Westwick) are another couple who hooked up and broke up over and over again, but ended up together in the end. Their worst breakup happened after she learned that he had gifted his creepy uncle a night with Blair in exchange for ownership of the hotel. Yes, really, and they still got married in the series finale. That's life on the Upper East Side, kids!

19 | Mindy/Danny, The Mindy Project

Chris Messina returned in a recurring role in the final season of The Mindy Project, paving the way for this couple's ultimate reconciliation. Before that, however, they had a painful breakup, necessitated by Mindy (Mindy Kaling) realizing that Danny expected her to be a stay-at-home mom to their child.

20 | Stefan/Elena, The Vampire Diaries

Here's the thing: Stefan and Elena broke up multiple times over the course of The Vampire Diaries, and it always hurt. The first one might sting the most, as it showed how incredible Paul Wesley and Nina Dobrev are at crying.

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21 | Fleabag/The Priest, Fleabag

While it's heartening to watch Fleabag (Phoebe Waller-Bridge) start to heal from some of the grief and shame that plagues her throughout the first season of the show, she does it by falling for someone ultimately unattainable. Though The Priest (Andrew Scott)—or "The Hot Priest," as viewers have dubbed him—decides that he can't give up his calling for her, he admits that he loves her too, making Fleabag's bus stop scene one of the most heartbreaking fictional splits ever and a new high watermark for series finales.

22 | Jimmy/Kim, Better Call Saul

No Breaking Bad fan could have expected that the spinoff/prequel series would be a love story, but the origins of Bob Odenkirk's Saul Goodman (once Jimmy McGill) are deeply rooted in his relationship with Kim Wexler (Rhea Seehorn). They don't break up because they don't love each other anymore; Kim calls it off because she realizes how destructive they are together. The series finale brought the former couple some closure, jumping to after the events of Breaking Bad, but this one still stings.

23 | Ted/Michelle, Ted Lasso

In the first season of Ted Lasso, we find out that part of the reason that Ted (Jason Sudeikis) took the Richmond job is that his wife, Michelle (Andrea Anders), wanted some space. When she and their son come to visit, Michelle confirms that she wants that permanently, initiating a divorce that throws Ted into a depression, even though he wants to see her happy. Even worse, this scene is intercut with one that shows something sparking between Roy (Brett Goldstein) and Keeley (Juno Temple) in the team's parking lot, after Ted says that he and Michelle met for the first time in a similar place.

24 | Crowley/Aziraphale, Good Omens

The fact that neither Crowley (David Tennant) nor Aziraphale (Michael Sheen) even realized they were a couple until their breakup in the Season 2 finale of Good Omens doesn't make it any less devastating. The demon and the angel assigned to live on Earth had been a package deal for so long that they took it for granted, the truth only bubbling up when Aziraphale betrays Crowley by agreeing to start actively working for the (corrupt!) people upstairs again. Fans are counting on the upcoming third season to fix it.

25 | Connell/Marianne, Normal People

The TV adaptation of Sally Rooney's book Normal People was a breakout moment for both Paul Mescal and Daisy Edgar-Jones, and it's no wonder, given their performances as two people (soulmates, most likely) who move in and out of each other's lives over a number of years. Connell and Marianne's relationship is plagued by poor timing and things left unsaid, and just when you think they've finally got it together, life throws another wrench between them. The last time, though, they part with their eyes wide open, and there's hope that they'll come back to each other sometime after the credits roll.

This story has been updated to include additional entries, fact-checking, and copy-editing.