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The 25 Saddest Breakups on TV

Rory and Dean
Source: CW

Jan. 28 2015, Updated 2:10 p.m. ET

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The best part about watching TV? Getting so invested in the characters that you feel like they're your BFFs.  We feel your pain. Here's 25 of the most depressing breakups in the history of scripted television. Word to the wise: Grab some tissues.

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Ross and Rachel

Ross and Rachel
Source: NBC

Ross and Rachel on Friends were on and off more than any other TV couple ever, but each breakup made us just as sad as the last. Yup, even when they were "on a breaaaak!"

Betty and Don Draper

Betty and Don
Source: AMC

Even though on Mad Men, Don was cheating on his wife, Betty, with other women, their eventual divorce was still kind of sad, right?

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Yang and Burke

Yang and Burke
Source: ABC

Grey's Anatomy is notorious for its breakups, but when Burke left Yang at the altar in the season 3 finale...nope. Couldn't handle it. Can't even talk about it.

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Ezra and Aria

Ezra Aria
Source: ABC Family

Honestly, Ezra and Aria of Pretty Little Liars were doomed from the start considering he was her high school teacher. But when she found out he had a son out of wedlock? Split. Just wait till she finds out he's "A"...

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Chuck and Blair

Chuck and Blair
Source: CW

Chuck and Blair were the only Gossip Girl couple who really made sense. Their breakups felt like our breakups. But thank the lord these two ended up happily ever after in the series finale.

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Carrie and Aidan

Carrie Aiden
Source: HBO

While it's not as intense as a post-it note, Carrie telling Aidan on Sex and the City that she didn't want to be engaged to him anymore broke our hearts. And then when they ran into each other on the streets years later and he had kids and she had Big? Ugh. Dead.

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Danny and Vicky

Danny Vicki
Source: ABC

And speaking of broken engagements, Danny and Vicky's on Full House was beyond depressing. After four months of being engaged, they broke up when Vicky got offered her dream job as a weather reporter in New York.

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CeCe and Schmidt

Cece and Schmidt
Source: Fox

New Girl's Schmidt really messed this one up. CeCe dumped him when she found out he was also dating Elizabeth at the same time! Any girl would've done the same but seriously, Schmidt. This is all your fault and we hate you for it.

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Michael and Holly

Michael Holly
Source: NBC

Even though Michael and Holly of The Office probably weren't soulmates, we can't help but shed a tear or two at the thought that she left him for Colorado and never came back. Really though?

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Seth and Summer

Seth and Summer
Source: Fox

Another tumultuous couple was Seth and Summer of The OC but at least they had a happy ending (and a wedding!)

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Brittany and Santana

Brittany Santana
Source: Fox

Brittany and Santana of Glee broke up for good right before Santana graduated from McKinley because Brittany wanted her to have the opportunity to be with a "real lesbian" in college. Ah, true love.

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Joey and Pacey

Joey and Pacey
Source: CW

Remember when Pacey broke up with Joey on Dawson's Creek before she left for college because he didn't think he was good enough for her? That was sad.

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Charlie and Marnie

Charlie and Marnie
Source: HBO

While not the most dramatic of the Girls breakups, Charlie and Marnie's split was still sad. Well, we mean the final split where they shared this cute, sad moment. Not the one where Marnie broke up with him because she wanted to see what else was out there.

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Cory and Topanga

Cory and Topanga
Source: ABC

Yes, we all know that Cory and Topanga get married (and have kids) in the end of Boy Meets World, but admit it—you cried so hard when they broke up the first time by the lockers in middle school and then realized what a mistake they'd made. It was heart-wrencking.

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Chris and Anne
Source: NBC

Considering the actors who play both Chris and Anne on Parks & Recreation won't be returning next season, their breakup wasn't that surprising, right? Was still so sad though.

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Peyton and Jake

Peyton bryan greenberg
Source: CW

On One Tree Hill, Jake broke up with Peyton after he heard her mumbling in her sleep that she still loved Lucas. I mean...that'll do it.

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Leonard and Penny on Big Bang Theory

Leonard and Penny
Source: CBS

Note to dudes—saying "I love you" too soon could totally ruin a relationship. That's what did in Leonard and Penny on Big Bang Theory.

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Rory and Dean

Rory and Dean
Source: CW

High school sweethearts breaking up is the most terrible thing, which is why when Rory and Dean split on Gilmore Girls (he accused her of paying too much attention to Jess), we sobbed endlessly. Dean ended up cheating on his wife with Rory later on, but still, really, really sad breakup.

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Winnie and Kevin

Winnie and Kevin
Source: ABC

Fact: Winnie and Kevin's Wonder Years breakup reminded you of your first true love lost.

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Jack and Avery

Jack and Avery
Source: NBC

The breakup of Jack and Avery on 30 Rock is sad depending on who you ask, but they both cheated on each other, him with her mother! That's just asking for it.

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Brenda and Dylan

Brenda and Dylan
Source: SOAPnet

The eventual breakup of Brenda and Dylan of Beverly Hills 90210 was really complicated, but him cheating on her with her BFF, Kelly, while she was abroad probably had something to do with it.

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Mindy and Casey

Mindy and Casey
Source: Fox

From the start, Mindy and Casey of The Mindy Project didn't seem like soulmates, but still, when they ended their engagement after he decided to stay in Haiti and she at her job in New York, our hearts broke a little.

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Grace and Leo

Grace and Leo
Source: NBC

Everyone cried when Will & Grace's Grace Adler's marriage to her dream man—a handsome Jewish doctor—ended in divorce since he cheated on her while overseas on a work trip.

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Sarah and Mark

Sarah and Mark
Source: NBC

Basically, what you need to know about Sarah and Mark's Parenthood breakup is that she chose another guy, Hank, over Mark. Ugh. Third parties are just the worst.

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Buffy and Angel

Buffy and Angel
Source: CW

Buffy (as in Vampire Slayer) lost her virginity to Angel, which caused Angel to go back to being evil. Wouldn't you break up with a guy if that happened to you?

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