The Most Toxic TV Couples Of The Early 2000s

If there’s one thing you could count on in the early 2000s, it’s that every popular TV show would have at least one toxic couple. The jealousy, miscommunication, and erratic behavior wouldn’t win these duos any relationship awards IRL, but they made the programs unmissable. Whether you were keeping tabs on Carrie and Big’s latest falling out or questioning whether Ted and Robin would ever get together, becoming invested in these couples was pretty much inevitable — not to mention, if you weren’t caught up, you were severely limiting your ability to make small talk with your friends.

Even now, 20 years after these couples were first introduced to the small screen, references to their romances are everywhere. The #deanandrory hashtag has 82 million views on TikTok, an app that was launched nine years after Gilmore Girls wrapped. The hashtag #chuckandblair has over 595 million views; Gossip Girl ended only four years B.T. (before TikTok).

Whether you’re currently revisiting your toxic faves from the early aughts or discovering them for the first time, here are the top 12 TV couples that put the mess in messy.

Chuck & Blair In Gossip Girl

The quintessential toxic couple: Chuck Bass and Blair Waldorf. Two deeply flawed, Machiavellian characters whose passionate, combative love story made Gossip Girl a must-watch for six seasons. Chuck and Blair were constantly playing with each other’s emotions, competing to have more power and control. They had a lot of bad moments, but potentially the worst was when Chuck traded Blair for a hotel in a deal with his Uncle Jack in Season 3. Yet, somehow, by Season 6, fans were relieved when they tied the knot.

Dean & Rory In Gilmore Girls

Despite Rory Gilmore telling Dean Forester that he was the “greatest boyfriend alive” when they ran into each other in Gilmore Girls: A Year In The Life, their romance was messy at best. Some not-so highlights: Dean broke up with Rory when she wasn’t ready to say “I love you” back; Dean told her he “couldn't care less” about Harvard when she was stressed about her application and canceled their date night; Rory cheated on Dean with Jess (and then crushed on Jess from afar instead of dumping her boyfriend); and when they had sex for the first time, Dean was married to someone else. Suffice it to say, “greatest” is not the first word anyone would use to describe this relationship.

Carrie & Big In Sex & The City

Carrie Bradshaw might have been a sex and dating writer, but her romantic life wasn’t exactly worth copying. Her tumultuous relationship with Big, which plagued her most of the show, was hardly aspirational. From her constantly trying to push him into a relationship to him deciding to move to Paris without giving her (his girlfriend!) a heads up, their romance was fraught with tension. Lest we forget that Big cheated on his wife, Natasha, with Carrie — and that she returned the favor by cheating on Aiden with Big.

Bette & Tina In The L Word

Bette Porter and Tina Kennard’s relationship in The L Word was full of problems. After Tina miscarried their baby in Season 1, Bette pursued an affair — something Tina eventually caught onto when she spotted them holding hands. The confrontation that followed this revelation was beyond toxic: Tina slapped Bette, and then Bette sexually assaulted Tina. (One fan of the show on Reddit referred to the moment as “the rape scene we were all supposed to be OK with.”) Though they took a break from each other afterward, this assault did not mark the end of their relationship — they continued to see each other, on and off, for the rest of the series.

Ryan & Kelly In The Office

The Office is more comedy than romance, but the relationships in the show have left their mark just the same. One couple who was potentially even more iconic than Pam and Jim? Ryan Howard and Kelly Kapoor, obviously. Unlike Pam and Jim, these two were not a pair you’d want to emulate. A brief overview: At one point, Kelly pretended to be pregnant to get Ryan’s attention. At another, Ryan sabotaged Kelly’s relationship with Darryl Philbin — only to instantly lose interest when Kelly broke up with Darryl. They were toxic with a capital T, but they seemed to get off on their own drama.

Joey & Dawson In Dawson’s Creek

Even as friends, Joey Potter and Dawson Leery were co-dependent. When they started dating, that unhealthy relationship dynamic only became more obvious. They were constantly fighting — so much so that it’s hard to believe they were ever buddies. There was also the distrust: Dawson stooped so low as to read Joey’s diary, and became angry with her when he read that she wasn’t a fan of his latest film project. Joey wasn’t innocent, either. When her co-worker unexpectedly kissed her at work, she opted not to tell Dawson. Their toxic behavior became even messier after their Season 2 breakup — the duo’s constant jealousy and game-playing made it clear that their romance wasn’t quite over (yet), but that didn’t stop either of them from pulling other SOs along for the ride.

Cristina & Burke In Grey’s Anatomy

From the start, Cristina Yang and Preston Burke’s romance wasn’t exactly a recipe for success. For one, he was the chief of cardiothoracic surgery, while she was starting as an intern. The power balance was always off between them, and as their relationship progressed, that only became more pronounced. When Burke proposed and Cristina said yes, she clarified that she wanted a small, non-religious wedding. Her requests went ignored by Burke, who started planning an elaborate ceremony that was the opposite of the dream wedding she described. He also decided to break up with her at said wedding, leaving her alone at the altar.

He explained his decision to her, “I'm up there waiting for you to come down the aisle and I know you don't want to come. I know you don't want to come, but you'll come anyway because you love me. And if I loved you, if I loved you, not the woman I am trying to make you be; not the woman that I hope you'll become; but you, if I did, I wouldn't be up there waiting for you. I would be letting you go.” His reasoning might have been OK, but his timing couldn’t have been worse.

Brooke & Lucas In One Tree Hill

Brooke Davis and Lucas Scott — Brucas, for short — were one of the more complicated couples in One Tree Hill. The fact that Lucas was in love with Brooke’s BFF Peyton Sawyer for years made rooting for Brucas somewhat of a lost cause. In the show, he cheated on Brooke with Peyton more than once, and infidelity wasn’t their only downfall. One of their worst moments? When Brooke thought she was pregnant, she compared Lucas to his deadbeat (and generally evil) father, Dan Scott. Afterward, Lucas not-so-kindly asked if she was sure he was even the father. Then, in a truly awful moment, Brooke decided to hurt Lucas back: She told him she was pregnant, even though the doctor had just called to tell her she wasn’t. And this all went down in Season 1, when their on-and-off toxic romance was only getting started.

Ted & Robin In How I Met Your Mother

Ted Mosby and Robin Scherbatsky’s relationship was doomed from the beginning (yes, even if — spoiler alert — they ended up together). On their very first date, Ted told Robin he loved her, something she rightfully considered a red flag. Throughout the show, their on-and-off romance had its share of unequivocally bad moments. At the end of Season 1, Robin invited Ted over while he was in a long-distance relationship with someone else, hoping to win him back. Ted then cheated on the same long-distance partner with Robin, lying to Robin and claiming he and his girlfriend had already broken up.

Whenever Ted and Robin actually were together, their romance underscored their incompatibility. From the very beginning, Robin made it clear she didn’t want kids, preferring to focus on her career. Ted, on the other hand, was much more invested in settling down, getting married, and having children. It was a fundamental issue they never could seem to agree on, making it hard to buy into Ted’s belief that they were meant to be.

Buffy & Angel In Buffy The Vampire Slayer

Buffy Summers and Angel first started seeing each other when she was 16 and he was 241 — not exactly the perfect foundation for romance. (A 225-year age gap isn’t anyone’s idea of healthy.) As a vampire, Angel had a long history of death and destruction, whereas Buffy was the slayer charged with, well, slaying the vampires of Sunnydale. Though they were natural enemies, that didn’t stop Buffy and Angel from falling for one another.

Unfortunately, the first time they had sex, he lost his soul and became a full-blown evil monster. Another less murderous issue? Buffy formed a dependent attachment to Angel, and when they eventually broke up, she even told her best friend, “Right now, I'm just trying to keep from dying... I feel like I can’t breathe.” Angel might have broken up with her for her own good (he is a literal vampire, after all), but his emotional unavailability yet constant presence was the hallmark of a toxic relationship. A classic case of breadcrumbing, if you will. It wasn’t Buffy’s only bad relationship, either — never forget her and Spike’s violence-filled romance.

Marissa & Ryan In The O.C.

Marissa Cooper and Ryan Atwood’s roller coaster of a relationship seemed to be constantly going awry. Marissa was the quintessential privileged, wealthy high schooler at the top of their school’s social pyramid. Ryan was the bad boy with major impulse control issues. Sometimes, opposites weirdly work together, but in this case, their mutual instability brought out the worst in each other, despite their best efforts. Throughout the show, Ryan was constantly trying to save Marissa and often became jealous of her guy friends. Not to mention, Marissa literally shot someone to save Ryan’s life in Season 3. There’s a reason that kind of high-stakes drama doesn’t happen in your typical high school romance — it’s too much for most adults to cope with, let alone two teenagers.

Betty & Don Draper In Mad Men

Betty and Don Draper may have looked like the perfect American couple, but their relationship was rotten to the core. As early as the pilot, the couple already showed signs of toxicity, as Don continued to stay in the city longer for work and compulsively cheated on Betty. (That’s not even getting into the fact that Don was lying to her about his true identity.) Instead of communicating to him that she felt stifled by suburban life, Betty just smoked, drank, and snapped at everyone around her until their eventual divorce at the end of Season 3. Even apart, the two fussed every time they saw each other and struggled to co-parent, all the way until the finale. They never had a moment that let audiences know there was something good, somewhere, that initially brought them together. A truly tragic, toxic TV marriage.