The 10 Most Tortured Romances On TV

TV is host to some of the most tormented romantic pairings of any medium. The long form story format allows writers to twist the knife in a star-crossed or otherwise doomed couple in every which way, so much so that invested "relationshippers" watching at home feel the pain just as much as the fictional characters.

The current crop of Sunday night shows could fill a list on its own (seriously, Boardwalk Empire? Homeland? The Walking Dead? Dexter?), but Complex look at the bigger picture, of series past and present, to give you the most absolutely agonizing relationships of all time. Read on for The 10 Most Tortured Romances On TV.

Written by Frazier Tharpe (@The_SummerMan)

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Portrayed by: Ted Danson and Shelley Long
Series: Cheers

The first sparks between the explosive couple were born out of bickering and even after they finally consummated their love-hate flirtation, Sam and Diane continued to spar. Most of the time their constant conflicts provided the heat that kept their relationship alive, but come finale time one would get fed up past the point of immediate reconciliation with the other, igniting an on/off pattern that continued until Long left the show after season five.

The mismatched pairing of womanizing athlete/bartender and intellectual waitress was always doomed, not because they couldn't commit to each other, but instead because they were too insecure to believe that the other would.

Portrayed by: Kristen Bell, Teddy Dunn, and Jason Dohring
Series: Veronica Mars

Let's get this out of the way first: Yes, we're aware that Veronica had a third boyfriend during the series' college season. We're just pretending that he, along with that whole portion of this otherwise brilliant show, didn't exist.

The high school years saw Veronica bounce back and forth between her trust fund boyfriends, Duncan Kane (Dunn) and Logan Echolls (Dohring). Her initial relationship with Duncan is marred by the revelation that she may be his father's illegitimate daughter, which understandably freaks them both the fuck out.

In the interim she's drawn to Logan, problem child and previously, her frequent antagonist. His self-destructive nature sends her back to Duncan, who eventually flees town for parts unknown (long story), opening the door for Logan to swoop back in by the end of the season (after spending a season railing the likes of hot cougar Charisma Carpenter).

That summary is exhaustive enough to warrant a spot on this list, but for the sake of space and time we haven't even mentioned the ways in which Veronica's date rape by a mystery assailant, the murder of her best friend—and Logan's girlfriend/Duncan's sister—Lily Kane (Amanda Seyfried), and Duncan's pregnant, comatose ex-girlfriend impact, affect, and inform the triangle. Trust us, though, for these three, tortured is an understatement.

Portrayed by: Katherine Heigl and Jeffrey Dean Morgan
Series: Grey's Anatomy

Grey's Anatomy, the reigning reveler of nighttime melodrama, has its fair share of tormented love affairs, but the series was arguably at its most soap operatic when Heigl's sexy Dr. Izzie Stevens fell for (and got engaged to) Seattle Grace heart patient Denny Duquette. It was painfully clear from their first meeting that Morgan would succumb to his heart condition at the most heartbreaking moment possible, and wouldn't you know it, he dies several hours after receiving a transplant.

The emotional agony of their relationship was manufactured and telegraphed but it had a lasting effect on audiences and Izzie herself, who would later suffer from metastatic melanoma and, as a result, regularly hallucinate a ghost Denny. Despite only lasting half a season, the love and loss of Denny Duquette cast a long shadow over Izzie's following relationships, and on the series overall.

Portrayed by: Kiefer Sutherland and Kim Raver
Series: 24

Is it wrong to say we enjoyed Jack Bauer's mid-series relationship with Department of Defense inter-agency liaison Audrey Raines more than his marriage to infamously doomed wife Teri? As sad and surprising as Teri's death was, she and Jack ultimately lacked in chemistry, perhaps because she and Jack spent like 90% of her run on the series apart.

The audience is compelled to root for Jack and Audrey as early as her first scene, because of what she represents for the embattled super-agent. At the time of her first appearance, Bauer has retired from the spy game for a healthier life in DC alongside Audrey's father, Secretary of Defense Heller (William Devane). Audrey is both a symbol of his escape and his reward, so naturally, with Jack's happiness riding on this relationship, everything must come crashing down, because Jack Bauer simply cannot know happiness for long.

Among Jack and Audrey's greatest hits: Jack forces CTU's only doctor at gunpoint to operate on a terrorist with vital information instead of her dying ex-husband, then Jack fakes his death for two years unbeknownst to Audrey, only to briefly choke her out when information implies that she might be in league with terrorists herself.

And when they finally get back on the same page? Jack is kidnapped by the Chinese government. It should have ended there, but the sixth season specialized in unnecessary plot developments, so Audrey Raines returned mid-season. It was revealed that before the government intervened she very stupidly went to China herself, where she was kidnapped and tortured into a skittish, psychologically damaged shell of herself. If you're exhausted, we don't blame you. Just know that that was the abridged version.

Portrayed by: Sarah Michelle Gellar, David Boreanaz, Marc Blucas, and James Marsters
Series: Buffy the Vampire Slayer

In a late-series episode of Buffy, the titular vampire slayer is diagnosed—by a vampire majoring in psychology, no less—with having an inferiority complex...about her superiority complex. That alone should sum up why each of her ill-fated relationships crashed and burned.

The first half of the series is centered around her and Angel (Boreanaz), an atypically star-crossed relationship: she's a slayer, he's a vampire, but he's a good one! With a soul and everything! The only problem is that he loses that soul and reverts to the diabolically evil creature he once was if he achieves true happiness, a development that they learn the, ahem, hard way, when they sleep together for the first time. Angel becomes the villain, cruelly using everything about his past relationship with Buffy against her in an attempt to break her down psychologically before killing her.

He's eventually re-ensouled and the relationship is repaired, but the experience gives Angel clarity to realize that it'll never work out and he splits town so she can pursue one that actually has a future. Enter Riley (Blucas), the corn-fed country dolt who happens to be the lead agent of The Initiative, a covert government operation designated to combat and study supernatural threats (read: demons). The short-lived couple crumbled quickly due to Riley's (boring) insecurities over both Buffy's strength and her casual approach to their relationship.

Loitering in the background during both of these romantic tenures is Spike, the sometimes ally yet otherwise evil vampire (with an endearing appreciation for contemporary delights like video games and buffalo wings). When Buffy dies at the end of the fifth season and is resurrected in the sixth, she returns with a self-loathing that spurs her to start an unhealthy, hate-fueled physical affair with the soulless vamp.

When she finally comes to her senses and breaks it off, his obsession with her drives him to attempted rape. He spends the entirety of the following season working to gain her forgiveness, and respect. She acquiesces, they share their first genuine moment and...Spike burns up in flames in a self-sacrificial act to save the world.

So there you have it. Shacking up with the admittedly sexy slayer will, in the long run, leave you an insecure mess, send you to Hell and out of town, or drive you to your death in your efforts to prove yourself worthy. She should come with a warning label.

Portrayed by: Jennifer Garner and Michael Vartan
Series: Alias

Sydney and Vaughn weren't star-crossed, nor mismatched personalities or anything like that. Theirs was a forbidden workplace romance, the kind where the boss puts a bullet in your head if he finds out.

When they first meet, Vaughn is Syd's CIA handler while she acts as a double for the company within the headquarters of diabolical terrorist cell SD-6. By the time they [SPOILER ALERT] successfully take SD-6 down, they've built up so much sexual tension that they nearly consummate their feelings right then and there during the raid with dozens of agents looking on.

The bliss is short-lived, though. In the tremendous cliff-hanger of the second season finale, Sydney wakes up in Hong Kong, with the events of the last two years completely missing from her memory. The first shocking reveal of what transpired during her absence: Vaughn got married. Cue an increasingly tortured, almost sadistic (on the writers' parts) game of one-step-forward-two-steps-back, as any victory the two achieve as a couple is offset by some horrible event, peaking with Sydney watching in horror as Vaughn is gunned down mere hours after learning they're going to have a baby.

Some criticized Alias' final moments as too saccharine for the oft-brutal spy drama; we say these two earned a lifetime of idle tranquility considering all they endured to get there.

Portrayed by: Katee Sackhoff and Jamie Bamber
Series: Battlestar Galactica

This relationship was only as hard as these two made it. And considering Kara and Lee are two very fucked up individuals, they made the prospect of being happy with each other extremely difficult.

Initially, their relationship is stuck in neutral because Kara was involved with Lee's late brother. Pretty soon, that excuse stops being valid, but any flirtation or further development is hindered by their own self-destructiveness. Case and point: After a one-night stand in which they confess their love for each other, Kara wakes up the next morning and marries someone else.

The love-loathing and mutual emotional destruction comes to a head when they literally beat the shit out of each other in the fleet's boxing ring—and then share a loving embrace, while their respective spouses watch with disgust. Apparently all of the couples therapists were nuked by the Cylons back in the series' pilot....

Portrayed by: Claire Danes and Damian Lewis
Series: Homeland

This is about as star-crossed as you get. Manic CIA analyst Carrie Brody is certain to the point of obsession that recently rescued POW Sgt. Nicholas Brody was turned by terrorists during captivity and is plotting an attack on the United States. She'll do anything to get close to him and uncover the truth, including sleeping with him.

One weekend getaway later and Carrie has fallen for Brody, while still holding true to her suspicions. Homeland hasn't even been on for two complete seasons yet, and still these two take the emotionally debilitating cake. Already their love saga has seen Carrie question her sanity and regularly blur the line between handler and asset and torrid love affair.

She's even confessed to fantasizing about him leaving his family, earning a magical pardon from the government for his non-actions, and running away together. And while Brody remains committed to his marriage, perhaps out of habit more than anything else, he can't help but admit that Carrie calms him, and, as someone who has also been traumatized by violent conflict, gets him in a way that no one else does.

By this point, a happy ending for the two would be the shocking twist, because there's almost no way it ends in anything less than heartbreak and turmoil for them. We'll see soon enough.

Portrayed by: David Duchovny and Natascha McElhone
Series: Californication

Where do we begin to describe this couple that has suffered just about every type of relationship scandal possible? Prolific author and boozing womanizer Hank Moody only drinks and sleeps around with assorted dimes when he's without his tether Karen, the love of his life and mother of his child. Seeing as boozing and womanizing are Californication's main activities, Hank is often untethered.

The series is less will-they-or-won't-they (get back together) and more when will they fall apart again, because anytime they achieve happiness, infidelity strikes (on Karen's part; Hank for all his faults, has never cheated), or Karen is engaged to another man, or a woman claiming to carry Hank's baby pops up, or that one time that Hank accidentally slept with a 16-year-old girl is revealed.

And each time, said scandal drives them apart within minutes, with Hank reverting to pining alcoholic and Karen returning to her flighty, siren ways, a dance they'll surely repeat every step of in the upcoming sixth season.

Portrayed by: Matthew Fox, Evangeline Lilly, Josh Holloway, Terry O'Quinn, Dominic Monaghan, Michael Emerson, Elizabeth Mitchell, Ian Somerhalder, Maggie Grace, Jorge Garcia, Daniel Dae Kim, Yunjin Kim, Emilie de Ravin, Henry Ian Cusick, Sonya Walger, Michelle Rodriguez, Jeremy Davies, Rebecca Mader, Nesetor Carbonell, Kiele Sanchez, Rodrigo Santoro, Harold Perrineau, Naveen Andrews

If you think we're being hyperbolic, clearly you haven't seen enough of this show. In addition to emotionally draining daddy issues, literally every adult main cast member on LOST had at least one tortured romance at one point or another, whether told through flashbacks, the on-island present, flash forwards, and yes, even the flash sideways.

Sure, the love triangle involving Jack (Fox), Kate (Lilly), and Sawyer (Holloway) was the main course, but if you watched the series, in a few short minutes you'll recall that all of the side drama you probably forgot about is equally tormented.

Remember the reveal that hateful half brother and sister Boone (Somerhalder) and Shannon (Grace) once had a one-night stand? Locke's epic saga of love and loss with Helen (Katey Sagal)? How about the time Charlie (Monaghan) lost his mind and almost drowned pseudo-girlfriend Claire's (de Ravin) baby?

Sawyer and Juliet (Mitchell)—whom Ben (Emerson) secretly nursed a homicidal, unrequited thing for once upon a time—would later morph the main triangle into a complicated rhombus. Sayid (Andrews) embarked upon a still-ridiculous island affair with material girl Shannon, in addition to nursing an age-old longing for his childhood friend Nadia. Then there's the epic, decades-, continents-, and dimension-spanning love story that is Desmond (Cusick) and Penny (Walger), which became an even bigger deal than Jack and Kate.

We could go on and on, but by now you get the idea. The only couple happy on this series was jovial old married couple Rose and Bernard. And they even had that one episode that was rife with strife.