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The 25 most toxic fictional couples of all time
HBO

The 25 most toxic fictional couples of all time

Sometimes love comes with a little -- or a lot -- of dysfunction. The endings are usually happy, but in a fictional sense, they can be highly entertaining. Here's our rankings of the top 25 totally fictional relationships of all time.

 
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25. Kevin and Winnie (The Wonder Years)

Kevin and Winnie (The Wonder Years)
ABC

This beloved ABC coming-of-age sitcom (set in the 1960s and '70s) that ran from 1988 to '93 got it right in the end. Kevin Arnold (Fred Savage ) and Winnie Cooper (Danica McKellar) were best friends. Yes, the series ended with the two as a couple, seemingly destined to be together. But they were never quite appealing as a couple. Mainly because Kevin was not likable once he started dating, he became too cool for his own good. Unlike the authentic nature of his character, he carries a torch for Winnie, showing off his vulnerability and insecurity amid the quest. So, the fact that the two went off in separate directions after high school, and Kevin ended up married to an unnamed woman and started a family, while still good friends with Winnie, provided perfect closure. 

 
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24. Ralph and Alice Kramden (The Honeymooners)

Ralph and Alice Kramden (The Honeymooners)
Jackie Gleason Enterprises; CBS Productions

If this were a modern-day couple, Ralph (Jackie Gleason) and Alice (Audrey Meadows) would have been divorced in a year. However, this was back in the day when couples stayed together no matter what. Ralph can be hilariously overbearing and hot-headed, but the real boss of the household was Alice — no matter how much Ralph wanted to send her "to the moon." Alice was there whenever Ralph needed to be reined in, cooled down, or brought back to Earth. Their toxicity was also quite endearing.

 
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23. Calvin and Beth (Ordinary People)

Calvin and Beth (Ordinary People)
Paramount Pictures

Things weren't always rough for the Jarretts, but that changed after the oldest son, Buck, died in a boating accident, where the younger son, Conrad, was present. That death and Conrad's subsequent suicide attempt and stay in a psychiatric hospital threw the family dynamic into shambles. Calvin (Donald Sutherland) became overprotective of his surviving son, much to the dismay of Beth (Mary Tyler Moore), who just wanted to quickly pick up the pieces and move on with some sense of normalcy within their upper-middle class north suburban Chicago bubble. Of course, Beth's insensitivity and inability to appreciate that she still had a husband and son to live with ultimately doomed her marriage in this Robert Redford-directed classic from 1980.

 
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22. Edward and Bella (Twilight saga)

Edward and Bella (Twilight saga)
Summit Entertainment

Yes, American teen Bella Swan (Kristen Stewart) and 108-year-old vampire Edward Cullen (Robert Pattinson) end up living relatively happy ever after. Now, they needed to have a daughter so Bella could become a vampire and keep Edward from wanting her human blood. Strange attraction breeds toxicity that probably should have been nipped in the bud by Bella's adult figures. Then again, all that drama and angst made for one of the most popular franchises of all time. 

 
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21. Kyle and Max (Living Single)

Kyle and Max (Living Single)
YouTube

A fun example of when "frienemies" find love -- with each other. Maxine "Max" Shaw (Erika Alexander) and Kyle Baker (T.C. Carson) loved throwing barbs back and forth at each other. So much so that those hilarious exchanges put them in bed together. Of course, the two could never make that love last  -- at least not within the confines of Living Single. However, as it turned out, the two had a child together when Max's sperm donor turned out to be Kyle.  

 
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20. Cliff and Janet (Singles)

Cliff and Janet (Singles)
YouTube

Toxicity tends to exist when one half of a couple  -- Janet Livermore (Bridget Fonda) -- is way more into the other half -- Cliff Poncier (Matt Dillon) without reciprocation. In this case, Janet is a fan girl of the widely panned rocker Cliff from this Cameron Crowe early-1990s hit. However, both are immature and insecure when it comes to matters of the heart, but they are quite entertaining within the confines of the Seattle grunge scene. 

 
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19. Bette and Tina (The L Word)

Bette and Tina (The L Word)
Showtime

Talk about ups and downs. Bette (Jennifer Beals) and Tina (Laurel Lisa Holloman) were all over the place as a couple during the run of this successful Showtime series. From the moment they met, the physical attraction was undeniable. However, the complexity of their respective lives seemed to hinder the staying power of their relationship. Perhaps that's why it made for exceptional dramatic television.

 
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18. Cam and Mitchell (Modern Family)

Cam and Mitchell (Modern Family)
ABC

Let's set the record straight: There are times when toxicity within a relationship works. Sure, it can be uncomfortable to watch at times, but in the end, we know it's going to work. From the very first episode of this massive ABC hit, we could not get enough of Mitch (Jesse Tyler Ferguson) and Cam (Eric Stonestreet). Whether hysterically fretting over baby Lily (at least in the beginning), to Cam's flair (remember Fizbo?) for the dramatic, to Mitchell's hilarious issues with his father and sister, they remained the highlight of the show's lengthy run. Their two-part wedding episode in Season 5 is considered one of the most important moments not only in the series' history but also in network TV history.

 
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17. Angel and Buffy (Buffy The Vampire Slayer)

Angel and Buffy (Buffy The Vampire Slayer)
Warner Bros.

Buffy Summers (Sarah Michelle Gellar) went through plenty of relationships during the course of this popular series (1997-2003). However, Angel (David Boreanaz) will always be her one true love. The two dealt with a lot, with Buffy essentially helping him move on from his violent vampire ways and feel comfortable doing good despite being the arms of a slayer. In the end, though, Angel knew Buffy deserved better, and he went to hell for her in order to save the world. They ultimately broke up with Angel, knowing Buffy needed to lead a normal life. That's all quite heavy for young love.

 
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16. Gary and Brooke (The Break-Up)

Gary and Brooke (The Break-Up)
Universal Studios

A couple breaks up early in the film, leaving the audience wondering whether they might get back together. The uniqueness of this 2006 romantic comedy-drama is that Brooke Meyers (Jennifer Aniston) and Gary Grobowski (Vince Vaughn) continue to live in the same condo after their breakup. Now, while both come to terms with the reasons for the initial breakup (Gary's childish antics and taking the somewhat pestering Brooke for granted), the idea of the two getting back together never seems plausible. After the condo is sold and each goes their separate ways, they meet on the streets of Chicago, enjoy a pleasant conversation, and smile as they move on -- perhaps with the possibility of giving it another shot. Yet, it's likely neither has really changed.

 
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15. Chandler and Janice (Friends)

Chandler and Janice (Friends)
YouTube

Chandler Bing (Matthew Perry) eventually ended up with long-time friend Monica, but watching the dysfunction of his hardly-ever-on, usually-off-again relationship with Janice Hosenstein (exceptionally played by Maggie Wheeler) was so much fun to watch. While Chandler had his well-documented insecurities, Janice is more annoying than anything. From her nasally voice to her machine-gun laugh, Janice is like nails on a chalkboard. That's why Chandler pretended he was relocating to Yemen to get away from her. 

 
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14. Alex and Piper (Orange Is the New Black)

Alex and Piper (Orange Is the New Black)
Netflix

Sure, there were plenty of toxic moments between Piper Chapman (Taylor Schilling) and Alex Vause (Laura Prepon), aka "Vausman," but they are truly among the great fictional couples of all time. And, they should earn a high grade for trying to make it work while in prison. There were plenty of ups and downs for the pair, but their love eventually endured, even while viewers wondered if they could even survive a single episode.

 
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13. Ross and Rachel (Friends)

Ross and Rachel (Friends)
The WB Television Network

Let's be totally honest --  Ross (David Schwimmer) and Rachel (Jennifer Aniston) were more annoying than cute. Still, their on-again, off-again relationship was always part of the storyline throughout the legendary show's lengthy run. They had plenty of memorable moments, whether off or "on a break." And, yes, Rachel was far too pretty and savvy to fall for a nerdy guy like Ross. Yet, in true Hollywood fashion, and through all the goofiness, it was only fitting that they would be together when it came time for the series to end. 

 
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12. Boon and Katie (Animal House)

Boon and Katie (Animal House)
YouTube

The romantic subplot between Boon (Peter Riegert) and Katy (Karen Allen) got annoying at times and was highly dysfunctional, but nonetheless important to the storyline of this classic 1978 farce from National Lampoon. The romance seemed doomed by the movie's end, but they did make up after party-boy Boon took Katy for granted enough to go cheating with her creepy philosophy professor. As the end of the movie states: "Boon and Katy Married 1964. Divorced 1969."

 
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11. Sam and Diane (Cheers)

Sam and Diane (Cheers)
NBC

Sam Malone (Ted Danson ) is a ladies' man who was never meant to settle down. So, it was no surprise he didn't find everlasting love with either Diane (Shelley Long). The oil-and-water relationship made for entertaining television, but Diane seemed helpless at times to get Sam to be serious. In the end, Sam's true love was his bar. Cheers was the only thing he could be faithful to and command his full attention toward. And, it was the perfect way to conclude one of the greatest sitcoms of all time.

 
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10. Dylan and Brenda (Beverly Hills, 90210)

Dylan and Brenda (Beverly Hills, 90210)
90210 Productions; Propaganda Films; Spelling Television

Brenda Walsh (Shannen Doherty) and Dylan McKay (Luke Perry) made for one of the most beloved fictional teen couples in network television history, but they never seemed destined to be together forever due to their collective dysfunction. Dylan couldn't make up his mind between Brenda and Kelly ( Jennie Garth), and was not reliable in many other aspects of his tortured life. Meanwhile, Brenda's dream of independence and of becoming an actress also played a part in why these 1990s lovebirds couldn't make it work. Sadly, Perry and Doherty have both passed on, but their 90210 legacy will live forever.

 
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9. Barney and Robin (How I Met Your Mother)

Barney and Robin (How I Met Your Mother)
CBS

As the rather disappointing end to this popular CBS sitcom came to an end, viewers learned that Robin (Cobie Smulders) and Barney (Neil Patrick Harris) had divorced a few years after being married. It's not surprising, but rather heartbreaking, since that was the most entertaining couple on the show -- good and bad -- and arguably the love of each other's lives. Yet, while fun to watch, the relationship never made sense and was essentially doomed from the beginning.

 
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8. Jesse and Jane (Breaking Bad)

Jesse and Jane (Breaking Bad)
ABC

It can certainly be argued that the love story between Jesse Pinkman (Aaron Paul) and Jane Margolis ( Krysten Ritter) was more tragic than toxic during their Season Two arc. Of course, when drug abuse eventually defines the relationship, the toxicity level rates high. Jane's heroin relapse also fed Jesse's addiction and ultimately cost her her own life. Of course, her disdain for Walter White didn't help ease Jesse's psyche.

 
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7. McDreamy and Meredith (Grey's Anatomy)

McDreamy and Meredith (Grey's Anatomy)
ABC

One of the most chronicled and talked-about couples in television history. Yet, professional critics did not necessarily care for this relationship, but all the dysfunction enthralled fans of the popular show. For viewers, the couple generated a love-hate relationship. Fans really wanted Meredith (Ellen Pompeo) to find true love, but should she really end up with the man known as Derek "McDreamy" Shepherd (Patrick Dempsey)? Their relationship was beyond complex  , and the force that drove the show for several seasons. 

 
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6. Mr. Big and Carrie (Sex and The City)

Mr. Big and Carrie (Sex and The City)
New Line Cinema; HBO

During the long run of this massively popular HBO series, the relationship between  Carrie (Sarah Jessica Parker) and "Big" (Chris Noth), aka James Preston,  was a prominent storyline. Carrie endured her share of failed relationships, and her run with Big could be exhausting. However, we knew he was the one love she could not shed, and she was the one who completed his life, even if they both tried to mess all that up with some petty musings and stereotype misunderstandings. They stayed together until the end when Big died of a heart attack in the HBO Max revival And Just Like That... 

 
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5. Rory and Logan (Gilmore Girls)

Rory and Logan (Gilmore Girls)
Netflix

Rory Gilmore (Alexis Bledel) enjoyed a trio of prominent love interests throughout the run of the iconic CW series. There was first-love Dean and bad-boy Jess, who challenged her like no other. However, her most serious adult relationship came via Logan Huntzberger (Matt Czuchry), whom she met at Yale and dated late in the series, and had an affair with during the "A Year in the Life" revival. Unlike Jess, Logan is a wealthy bad boy who often took Rory for granted and made her live out of her comfort zone -- for better or worse. Though mostly the latter.  

 
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4. Elaine and Puddy (Seinfeld)

Elaine and Puddy (Seinfeld)
NBC

The on-again, off-again extended fling between Elaine Benes (Julia Louis-Dreyfus) and David Puddy (Patrick Warburton) was one of convenience. And, as Jerry said, viable because "clearly, no one else can stand to be with either one of you." Fan of the "high-five," Arby's and, of course, the New Jersey Devils, the mechanic-turned-car salesman, could be laid back and sympathetic but also passionate and downright strange while staring into nowhere. He and Elaine were known to break up multiple times a day. The couple's actions were also disturbed by clergy, co-workers, and essentially every human on the planet.

 
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3. Nate and Maddy (Euphoria)

Nate and Maddy (Euphoria)
HBO

There really isn't anything truly healthy when it comes to the inconsistent relationship between popular cheerleader Maddy Perez (Alexa Demie) and often-abusive Nate Jacobs (Jacob Elordi) from this acclaimed HBO series. In a lot of ways, though, their relationship is textbook dysfunction. Nate's underlying sexual and emotional issues lead to his volatile and controlling nature toward Maddy, who struggles to differentiate true passion from Nate's physical and sexual abuse. In many ways, these tainted figures are made for each other. 

 
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2. Mickey and Mallory (Natural Born Killers)

Mickey and Mallory (Natural Born Killers)
Warner Bros.

Got to hand it to Mickey (Woody Harrelson) and Mallory (Juliette Lewis) Knox, they were so in love and deranged that they didn't realize -- or care -- that their relationship was toxic. Then again, that would be the case when you are also a serial killer from this infamous 1994 Oliver Stone offering. Trauma and abuse littered the childhood of each character, thus paving the way for their future. Mickey and Mallory have their moments of some deserved empathy, but in the end, they are way over the top. One can thank Mr. Stone for that.

 
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1. George and Susan (Seinfeld)

George and Susan (Seinfeld)
NBC

How can George Costanza (Jason Alexander) and Susan Ross (Heidi Swedberg) not top this list? George essentially killed Susan by getting her to agree on cheap wedding invitations, which caused her death after she continuously licked the toxic glue on the envelopes. What a way to end a relationship that was a joke to begin with. Come on, because of George, directly or indirectly, Susan was thrown up on (Kramer), had her father's cherished cabin burn down (again, Kramer), got fired from a high-paying NBC job, turned her to lesbianism, and ultimately ended her life. 

Jeff Mezydlo

A Chicago native, Jeff Mezydlo has professionally written about sports, entertainment and pop culture for parts of four decades. He was an integral member of award-winning sports sections at The Times of Northwest Indiana (Munster, Ind. ) and Champaign (Ill

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