Love is awesome. Until it goes bad. Then, it’s not so great. This remains true on television, where the freedoms of storytelling often make the standard breakup into a situation that is truly spectacular in its horribleness. The following are 25 of the most epic of TV breakups.

#25 Bones: Booth and Hannah

He bought her the biggest, flashiest diamond ring on the planet. But she didn’t want to marry him. As a result, the oft-heartbroken Booth lost both his girl and his ring (throwing it into the water was a singularly foolish and expensive choice). And the audience was left to wait for the wounds to heal before Booth could move on to the more appropriate choice of Brennan.

Bones: Booth and Hannah

#24 Supernatural: Dean and Lisa

After averting Armageddon and witnessing the death of his brother, Dean at least got the comforts of home with his beloved Lisa and her son Ben. Unfortunately, Dean later got briefly vampirized. In his attempts to nobly Twilight out of the relationship (for her sake, of course), Dean went all threatening and scary. That and a poorly-timed truthful moment led to the disappearance of Dean’s home life from the Supernatural world.

Supernatural: Dean and Lisa

#23 Lost: Jack and Kate

It’s not like it was unexpected, but Jack and Kate’s breakup still managed to shock. Kate’s unreasonable need for secrecy was never so pronounced, and Jack’s quick descent into island-withdrawal insanity hit suddenly. Their engagement then exploded with an atomic-bomb-dropped-into-a-Dharma-hatch force.

Lost: Jack and Kate

#22 Gilmore Girls: Lorelei and Luke

They broke up twice, but the second breakup was the true tragedy — for the audience anyway. When Luke refused to set a wedding date, Lorelei responded by running to the bed of Christopher. After that, we had to put up with a season of a pointless Lorelei-Christopher marriage and dragged-out romantic tension. Was Lorelei’s awesome karaoke performance to regain Luke worth it?

Gilmore Girls: Lorelei and Luke

#21 How I Met Your Mother: Lily and Marshall

They had the perfect relationship and were heading for the perfect wedding. It truly was all perfect until Lily realized she had never done anything else except be perfect in her relationship. So she ran away. To San Francisco. Leaving Marshall heartbroken on the stoop. Full reconciliation would take up the next season.

How I Met Your Mother: Lily and Marshall

#20 Raising Hope: Jimmy and Lucy

It wasn’t much of a relationship: a hook-up in the back of a van while Jimmy on his way to the store. But the ending made up for it. Having learned that Lucy was a wanted serial killer, Jimmy’s mom knocked her out with a TV. What little communication occurring between the couple afterwards was on Death Row. At least they got a baby out of it.

Raising Hope: Jimmy and Lucy

#19 Mad Men: Don and Betty

Years of infidelity weren’t enough to break up the most dysfunctional couple of the early 1960s. Destruction, however, was imminent when Betty found out that her husband was actually a guy named Dick. The name was possibly an apt description for both spouses…

Mad Men: Don and Betty

#18 Grey’s Anatomy: George and Callie

After a quickie Vegas wedding, George strayed from his marriage to Callie by sleeping with Izzie. The resulting break-up of the marriage was big, but the truly epic moment came when Callie went to confront the other woman, and Izzie thought the two were going to have a fist fight in the cafeteria. However inappropriately-behaved the surgeons of Grey’s Anatomy were, fist fights fortunately remained too much.

Grey’s Anatomy: George and Callie

#17 Roseanne: Roseanne and Dan

After his heart attack, Dan Connor needed to change his lifestyle or risk death. But he couldn’t resist snacking on junk food, leading to a massive marital argument. Roseanne started throwing all the food into the garbage, which led to Dan flipping over the coffee table. The fight escalated until Roseanne went away to Jackie’s. The breakup wasn’t permanent, but it was definitely an epic fight.

Roseanne: Roseanne and Dan

#16 Glee: Rachel and Jesse

You’d think that dumping Rachel in favor of his first, true love, Vocal Adrenaline, would be enough for the evil that was Jesse St. James. But no. He then had to bring his entire glee club over to haze the inferior New Directions. And then he lured Rachel into the parking lot where a fake reunion quickly devolved into an egg massacre.

Glee: Rachel and Jesse

#15 Friends: Ross and Rachel

We all remember the infamous words: “We were on a break!” When Ross cheated (or did he?) on Rachel in season 3 of Friends, and she called it off in one long, excruciating fight (while the rest of the gang hid in Monica’s bedroom and ate leg wax to sustain themselves) that ended in Ross sobbing at her legs and begging for forgiveness, they were a devastating epitaph on a relationship we’d all been rooting for, and a signifier of one of the show’s saddest, most emotional moments ever

Friends: Ross and Rachel

#14 Veronica Mars: Aaron and Lynn Echolls

His cheating was finally made public. Their son was getting into trouble and fighting with dad. So Lynn Echolls simply told her movie-star husband she’d had enough.

And then she jumped off of a bridge.

Veronica Mars: Aaron and Lynn Echolls

#13 True Blood: Sookie and Bill

Having just screwed his former lover’s head around (literally, and that’s not all he screwed), Bill dumped current-girlfriend Sookie for her own protection. It really, really didn’t work, since she came back for him and nearly got killed in the process.

True Blood: Sookie and Bill

#12 Gossip Girl: Blair and Chuck

In a move to get Chuck’s hotel back from his evil Uncle Jack, both Blair and Chuck told Jack they’d do anything to make it happen. Jack gave Blair an Indecent Proposal, saying Chuck could have his hotel back if Blair would sleep with creepy Uncle Jack. That was disgusting enough, but then when Blair decided to go through with it because of her love for Chuck, she found out that Chuck knew about and was in support of Jack’s plan — all so he could get his hotel back. Blair said goodbye to Chuck, and the hearts of “Chair” shippers everywhere shattered into a million pieces.

Gossip Girl: Blair and Chuck

#11 Lost: Desmond and Penny

Desmond really was going to propose to his true love, Penny. If only that annoying jewelry store woman hadn’t explained the concepts of fate and the future in so convincing a way, he might have gone through with it. Instead, Desmond wimped out, wasted the beyond-his-means ring and joined the army. It would take years and a whole bunch of boats before they rectified the breakup.

Lost: Desmond and Penny

#10 Six Feet Under: Nate and Brenda

It seemed like yet another chapter in their on-again-off-again relationship when Nate cheated on his pregnant wife and ended up hospitalized. He told her Brenda it was over, but the audience wasn’t likely to believe that story yet again.

Then Nate died of a stroke.

It was over.

Six Feet Under: Nate and Brenda

#9 Fringe: Peter and Olivia

When the girl of his dreams turned out to be an evil doppelganger from a parallel universe, Peter’s relationship went downhill fast. But she didn’t go quietly — Fauxlivia left murder and destruction in her wake as she went home. And it didn’t even end there…

Fringe: Peter and Olivia

#8 Gilmore Girls: Rory and Dean

Dean dumped Rory three times. But it was the second dumping that was the worst. Fed up with Rory’s interest in and flirting with Jess, Dean called it quits with Rory. Right in the middle of a dance marathon. Kirk then danced to victory while the rest of the universe sobbed.

Gilmore Girls: Rory and Dean

#7 Glee: Will and Terri

While searching for a pocket square, Will Schuester found his wife’s fake-pregnancy pad. Which led him to finally figure out that Terri was not, in fact, pregnant. This irritated Will. Following an intense and surprisingly physical confrontation, in which Terri pointed out that self-loathing was the cornerstone of their relationship, Will stormed off. Bye-bye dysfunctional marriage! Hello promotional mattress in the music room!

Glee: Will and Terri

#6 How I Met Your Mother: Ted and Stella

Ted thought he had found the woman of his dreams. Their almost-perfect romance led quickly to a weird but happy wedding. But it was not to be. Thanks to the presence of exes at the wedding, Stella ran off with a karate instructor and Ted was left alone. She wasn’t the mother after all.

How I Met Your Mother: Ted and Stella

#5 30 Rock: Liz Lemon and Carol Burnett

Thanks to flight issues, the formerly happy couple was on edge. Alas, Captain Carol chose to abuse his power over “fasten seatbelt” lights and such. The fight came to a head after about half an hour, when Carol pulled a gun on a mutinous Liz before she could escape via evacuation slide. The pair then realized that more than an old-man human shield had come between them. Can they still be friends? Probably not.

30 Rock: Liz Lemon and Carol Burnett

#4 The Bachelor: Jason and Melissa

During the 13th season of The Bachelor, leading man Jason Mesnick narrowed down his choices to Molly and Melissa. He chose Melissa. Then, for the “After the Final Rose” special, Jason changed his mind. Melissa found herself dumped on national television, and Molly became the lucky lady. Then ABC filmed and funded the wedding.

The Bachelor: Jason and Melissa

#3 Jersey Shore: Sammi and Ronnie

It’s not like this was ever a healthy relationship. But the recent blowup between the betanned Shore folk reached epic proportions of love-illness. After Sammi got to grinding with another guy at the club, Ronnie exhibited true maturity by going home to trash her room. Then there was much bleeped swearing. And Sammi left. Of course this meant that Ronnie wanted her back.

The breakup probably won’t stick — we may be in for this again. And again.

Jersey Shore: Sammi and Ronnie

#2 Sex and the City: Carrie and Berger

The relationship wasn’t great, but there can never ever be justification for Berger’s breakup with Carrie via post-it note.

“I’m sorry. I can’t. Don’t hate me.”

I’m sorry. I can’t. I still hate that breakup.

Sex and the City: Carrie and Berger

#1 Buffy the Vampire Slayer: Buffy and Angel

After a night of passion turned him into a soulless monster, Angel spent half a season destroying Buffy and the world. He was about to succeed when the soul magically returned, reuniting the true lovers. Alas, it was too late. Evil-Angel had opened a portal to hell that could only be closed with his blood. So Buffy had to stab her greatest love in order to save the world.

That’s got to suck.

Buffy the Vampire Slayer: Buffy and Angel

Laurel Brown

Senior Writer, BuddyTV

Laurel grew up in Mamaroneck, NY, Grosse Pointe, MI and Bellevue WA. She then went on to live in places like Boston, Tucson, Houston, Wales, Tanzania, Prince Edward Island and New York City before heading back to Seattle. Ever since early childhood, when she became addicted to The Muppet Show, Laurel has watched far too much TV. Current favorites include ChuckModern FamilySupernaturalMad Men and Community. Laurel received a BA in Astrophysics (yes, that is possible) from Colgate University and a PhD in Middle Eastern Studies and History of Science from Columbia University before she realized that television is much better than studying.