1. Smallville – Lana and Clark

Talk about a television romance with the world up against it. With a chemistry that seemed constructed by the gods, Smallville fans wanted nothing more than to see protagonists Lana and Clark together forever in romantic bliss. However, the writers weren’t going to give us that satisfaction so easily.  They used every trick in the book to keep the two apart, all while keeping the tension between them burning hot. 

Warner Bros. via IMDB

We finally got to see Clark and Lana become a couple in season seven. Sadly, this seven-year build up resulted in a very short relationship. Ultimately, Lana got infected with kryptonite and Clark’s ultimate love became his ultimate danger. Because, of course. With Lana banished from the show, writers were finally able to utilize Louise Lane as Clark’s ultimate love interest. 

2. The Fresh Prince of Bel-Air – Will and Lisa

While main character Will spent the majority of his time on the The Fresh Prince of Bel-Air chasing any girl that crossed his path, that all came to an end during the fifth season. That’s when we were introduced to Lisa Wilkes. With her arrival, we saw Will’s character evolve from an obnoxious teen to a man.

NBC Productions

Despite going through an array of ups and downs, we really thought that Lisa and Will were going to make it. She was there for him when he was attacked at the bowling alley and even stood by his side when he was hospitalized with a gunshot wound. However, during the season finale wedding special, she called everything off at the altar and left Will crushed. The sadness he conveyed felt so real that some of us are still coping with it. 

3. Cheers – Sam and Diane

Sam and Diane were the living incarnation of the old saying ‘opposites attract.’ Sam was the working class ball player turned bartender and Diane was the college-educated intellectual. Surprisingly, they made one ’80s TV’s most beloved couples. Their romance started rather predictably with the two of them driving each other up the walls. Nonetheless, by the end of the first season, all their friction melted into love. 

Paramount Television via IMDB

Their first onscreen kiss was the start of one of television’s rockiest relationships. In spite of their many trials, though, the two eventually planned to take the plunge and get married. Before they said ‘I do,’ however, Diane was offered a chance at making her career dreams come true, and Sam convinced her to halt the wedding. She promised to return in six months, but ended up being gone for six years, thus ensuing one of the saddest TV breakups ever. 

4. The Wonder Years – Kevin and Winnie

Nothing hits us quite as hard as our first love, and no two characters conveyed what a first relationship is better than Kevin and Winnie. Audiences followed a 13-year-old Kevin as he tried to win over the girl of his dreams. He pulled all the awkwardly endearing stunts one would expect a junior high teen to pull. Sometimes they paid off, and often times they didn’t. 

IMDB / New World Television / The Black/Marlens Company

Ultimately, he won over the heart of his beloved Winnie. However, much like in real life, their high school relationship was extremely turbulent. Their love for each other came up against jealousy, possessiveness and selfishness. Nothing was more relatable than the pain we saw them go through when the relationship finally ended. We’ve all been in their shoes, and watching them always manages to take us back to our first bouts with love. For the sake of a happy ending, the pair did end up getting back together in the show finale.

5. Gilmore Girls – Lorelai and Luke

Throughout the run time of the Gilmore Girls, we usually saw Rory jump in and out of relationships with men who weren’t right for her. It definitely pulled at our heartstrings to see a downtrodden Rory, but the real heartbreak stepped in when things began to crumble between Luke and Lorelai. The chemistry between the two had always been solid, and when they finally ended up together after five seasons it was what audiences had always been rooting for. 

Warner Bros. Television via IMDB

The beauty of this beloved duo stemmed from the fact that Luke and Lorelai really needed each other. When Lorelai’s ex Christopher stepped back into the picture and wrecked everything between her and Luke, fans of the show were crushed. Thankfully, we were all given the happy ending we hoped for, as Lorelai realized Luke was her proper soul mate.

6. Saved By The Bell – Zack and Kelly

Back in the 1990s, Kelly Kapowski was basically the poster child for the girl next door. When both male protagonists Zack and Slater fell in love with her, fans were right there with them. Setting aside our own feelings, Saved By The Bell fans everywhere knew that Kelly was meant to be with Zack. Throughout the show’s run time, he managed to scheme his way into her heart and eventually win her over. 

NBC Productions via IMDB

In our 1990s minds everything seemed right with the world. However, things weren’t ever smooth sailing for the couple. Zack screwed up this relationship more times then we could count. Every time things crumbled between them, fans had to relive the heartache of yet another tragic breakup. Ultimately, the writers knew what fans wanted to see and by the time the show wrapped in 1994, marriage was the only way to go for the two high school sweethearts. 

7. Full House – Steve and DJ

When it comes to the saddest TV breakups, one cannot leave out Steve and DJ from Full House. We didn’t get any of the dramatics with this breakup, instead we saw things slowly fall apart. In the beginning, the two were a powerful teenage unit. Sadly, that didn’t last very long. Once the initial heat died down, DJ realized that her and Steve had nothing in common. 

Warner Bros. Television via IMDB

It came as no surprise to viewers, who all noticed this way before DJ. As nice as Steve was, he was always kind of a doofus. Despite their major differences, they would drag their relationship along until there was nothing left. DJ eventually ended things with Steve and sent him on his way. However, in typical 1990s fashion, Steve popped up again on the last episode and we were left to assume that they lived happily ever after.

8. That ’70s Show – Eric and Donna

It seems that most TV shows in the 1990s presented us with one of those concrete couples that seemed unstoppable. We couldn’t imagine them splitting, and if they did, the world would have likely turned upside down. Amid the big curveballs of small screen romances, was that of That ’70s Show’s Eric and Donna. 

20th Century Fox Television via IMDB

The show’s power couple held strong until the very end of season seven. Amid the chaos of his own life, Eric ditched Donna and the crew and fled their native Wisconsin. We were heartbroken and not just because of the breakup, but because we were left with a forgettable final season with the addition of Randy, who was specifically added to the cast to act as an Eric replacement.

9. Friends – Ross and Rachel

One of the most recognizable and saddest TV breakups of all time was on Friends. During those early seasons, Ross and Rachel were everything. Ross had pined for her since his days as a high school nerd, but life finally gave him a real chance to be with her. Whenever the two would date other people, audiences would collectively cringe. The pair needed to be together and everyone knew it but them.

Warner Bros. Television via IMDB

When they finally became an item, it was an iconic television moment. However, all their happy moments were out shined by their breakup. Our hearts sank when they endured one of the most savage on-screen breakups, and the event packed such an impact that it’s still being debated today. Did Ross cheat on Rachel or were they really on a break? Either way, the Friends finale finally gave us the happy closure we’d been waiting as the two finally acted on their enduring feelings for each other.

10. Freaks and Geeks – Lindsay and Nick

Freaks and Geeks was one of the most beloved TV programs of the 1990s. It made quite a few waves for a show that only lasted a single season. The success surrounding Freaks and Geeks no doubt stemmed from its sincerity. The characters were written in a way that made them easy to identify with. We all knew a Nick and Lindsay growing up and that made them all the more dear to us.

Apatow Productions/DreamWorks Television via IMDB

At the start of the series, we were all certain that Lindsay would end up with Daniel. When the slightly geekier Nick stepped in and won her heart, it was a huge shocker. When the relationship ended, the two were both wrecked and the whole friend group was somewhat torn. Thankfully, the two both made peace and found a better path. Lindsay decided to follow a Grateful Dead tour and Nick ended up falling in love with another girl. 

11. The Sopranos – Tony and Carmela

Honestly, in the long run, Tony and Carmela’s split was probably best for everyone in the Soprano family. The infidelity, the secrets and lies all became too much at a certain point and we were just waiting for Carmela to snap. After more than a few savage arguments between the two, it finally happened and we cheered Carmela on as she kicked Tony out and forced him into his own small apartment. 

HBO via IMDB

However, this split didn’t come without its major sad points. AJ became more rebellious and Carmela had no control over him. She eventually sent him to live with Tony and was left all alone in a giant mansion. After half a season, Carmela and Tony managed to patch things up, but it came with quite a cost at the end of the series. 

12. Boy Meets World – Cory and Topanga

Cory and Topanga’s romance wasn’t exactly the most realistic portrayal of teenage love. In terms of maturity, they were light-years ahead of most real-life teens. That was exactly what made them so endearing, though. Seriously, just how the heck did a 15-year-old Cory explain the meaning of  love to a confused Topanga? Most adults don’t even know the true meaning. 

Michael Jacobs Productions/Touchstone Television via IMDB

While their relationship seemed solid through and through, they did go through a dark period during season five. Cory kissed another girl during a ski trip. When Topanga found out, she didn’t hesitate to end things with the love of her life. The rest of the season consisted of a heartbroken Cory moping around the school and trying to win her back. He eventually did, but their initial breakup still remains one of the saddest in TV history.  

13. Peep Show – Mark and Sophie

Mark had the hots for Sophie from the first episode of Peep Show. He was extremely awkward, she was somewhat shy and they seemed like they’d make for a perfect couple if the word perfect secretly meant extremely awkward. On the road to Sophie’s heart, Mark had to undergo his fair share of humiliation. This included his office rival Jeff dating Sophie and getting their intimacy rubbed in his face.

Objective Productions via IMDB

When they did finally get together, they realized that they were both settling for the worst. Mark was more awkward than ever, and Sophie did not take it well. Fittingly, the relationship came to an end on their wedding day. Both cried at the altar and hoped the other would call everything off. Before exchanging vows, Sophie booked it and ran out of the church.

14. Scrubs – J.D. and Elliot

Throughout most of the series, we were never treated to a serious relationship between J.D. and Elliot. They did become an item during the first season but it ended almost as fast as it started. It broke our hearts because inside we knew that they were made for each other. We were further saddened when the pair began exploring other relationships that were obviously destined for the rocks. 

ABC Studios via IMDB

The show further teased us when J.D. and Elliot explored the concept of friends with benefits. They would also wave touching moments in front of our faces and scenes where they’d rediscover their feelings for one another. Yet, in the end it would lead nowhere. In typical fashion, the show waited its last season for their romance to finally bloom in full. They got married, moved in together and even had a baby. The nine-year wait was so worth the emotional roller coaster, though. 

15. Roseanne – Darlene and David

The biggest romance in Roseanne was definitely the one between Darlene and David. The two fit together like a hand in glove. The sensitive young man was immediately embraced by the Connor family and even moved in with them. That’s definitely a rare occurrence when you compare it to any of Becky’s relationships. That said, David and Darlene’s relationship was no walk in the park. Throughout the series, the two makeup and breakup three times and each split is more dramatic and heartbreaking then the last.

Paramount Television via IMDB

While Darlene had the comfort of her family to fall back on, David was quite alone in the world and that made everything worse. While they do their fair share of bickering while together, nothing seemed right when they were apart. It is later revealed during the series finale that they ended up getting married and having kids. Unfortunately, we later learn during the show’s reboot that things again didn’t work out. That leaves for four sad TV breakups on a single series.

16. Twin Peaks – Donna and James

Twin Peaks is considered a show on a level of its own, and the fine character development can definitely take responsibility for that. While the main source of action usually centered on Special Agent Cooper, there were a bulk of side stories surrounding the central mystery around the murder of Laura Palmer. One of these followed Donna Hayward, Laura’s best friend. She was on a quest to get to the bottom of what happened to Laura. 

Spelling Entertainment/Twin Peaks Productions via IMDB

While on her quest for answers, she reconnected with Laura’s secret ex, James Hurley. Amid their work, attraction hit the pair and they became somewhat of a couple. It wasn’t all unadulterated bliss for the two, though, especially after James began having feelings for Maddy Ferguson. Eventually, trouble found James and he was forced to leave town. Before hitting the road, though, he professed his love for Donna, promising her that he’ll come back. The relationship was never mentioned again.

17. A Different World – Dwayne and Whitley

A Different World went through some drastic changes within its first two seasons. When the show began, male lead Dwayne Wayne seemed destined to ultimately end up with Lisa Bonet’s character Denise Huxtable. Once she left the show, Jasmine Guy’s Whitley took her place as the starring female lead. This led to one of those classic ‘opposites attract’ situations.

Lynn Goldsmith/Corbis/VCG via Getty Images

While Dwayne was just a normal guy, Whitley was an out-of-place Southern belle. She was snobby and out of touch with everyone around her. While this did result in a fair share of clashes between the two, they eventually fell in love and even planned on marrying. Sadly, it all came to an end when Dwayne confessed that he had gone out for coffee with another woman. The two went their separate ways, but eventually ended up together by the final season. Still, the sting of that initial breakup was never lost on audiences. 

18. Dawson’s Creek – Joey and Dawson

Out of every character on Dawson’s Creek, Joey had the most turbulent relationship history. While some might think of her time with Pacey as the most romantic and heartbreaking, nothing could have compared to the love and loss she experienced with Dawson. There was just so much more hanging in the balance.

Handout / Getty Images

They had a friendship stemming back to childhood. And transitioning that friendship into a relationship put those years on the line. At one point, Joey cancelled a year-long trip to Paris to be with Dawson, only to eventually cheat on him and end things. They didn’t automatically jump into friendship mode again after that. Things were bitter between the two for most of the series afterward. 

19. How I Met Your Mother – Marshall and Lily

While most people were focused on the love connection between Robin and Ted in How I Met Your Mother, fans knew they would likely not end up together as she was retrospectively referenced as Aunt Robin. When things ended with them, we just kind of accepted it. However, When Marshall and Lily had their miniature breakup on season one, our hearts broke in a thousand pieces.

20th Century Fox Television via IMDB

Seeing a sensitive guy like Marshall standing in the rain and clutching his wedding ring still pains us to think about. Lily eventaully came back six months later and the two did get married, but in the heat of the moment, we were definitely looking at one of the saddest TV breakups. 

20. Buffy The Vampire Slayer – Buffy and Angel

They were definitely every gothic teen’s favorite couple back in the 90s. Buffy was a vampire slayer and Angel was a vampire. Despite how badly we wanted things to work out between them, Angel had a lot going against him. For starters the title of the show alone predicts his fate. 

IMDB / Mutant Enemy / Kuzui Enterprises / Sandollar Television /
20th Century Fox Television

People who aren’t familiar with the show might wonder how a vampire slayer and a vampire got together to begin with. Firstly, Angel was a cursed vampire who had remorse and human soul. Once his curse was broken, Buffy had to cast her feelings aside and take care of business. As you can probably imagine, a lot of teen hearts were broken by this. 

21. Family Ties – Alex and Ellen

Apparently, trips to Paris have caused of a lot of TV’s saddest breakups. Back in the late 1980s, Alex and Ellen were one of the hottest couple on television. Women from all walks of life were charmed by Michael J. Fox and many a guy had spent his days daydreaming about being Ellen’s significant other. 

IMDB / Paramount Television / Ubu Productions

The show almost immediately established Ellen as a key part of the show after the two lovebirds met while studying at Leland University. Audiences got used to the idea of Alex having a significant other and tuned in week after week to see where their relationship was headed. Sadly, it ended up heading nowhere. Ellen got a dance scholarship to go to Paris and went her own way. 

22. Beverly Hills, 90210 – Brenda and Dylan

It’s been almost 20 years since Beverly Hills, 90210 was cancelled, yet images of Dylan and Brenda together still remain iconic to this day. Why? They were the prototypical bad boy/good girl 1990s couple. Likewise couples popped up throughout the decade but none of them were as beloved as Dylan and Brenda.

Spelling Television/Torand Productions

Sadly, these two high school sweethearts didn’t walk down the aisle. In typical bad boy fashion, Dylan ended up cheating on Brenda with her best friend Kelly while she was studying abroad. He eventually broke the news to her and their relationship came to a swift end. This all led to a slew of sulking Brenda episodes, but it was cool because we were sulking right there with her. 

23. The Big Bang Theory – Penny and Leonard

Anyone who’s watched The Big Bang Theory knew from the start that Penny and Leonard were meant for each other. After all, Leonard was the main character and Penny was the cute new girl in the apartment complex. Go back to episode one and you’ll see that tension was present from their very first meeting. As complete opposites, they fit the TV relationship mold to perfection.

IMDB / Chuck Lorre Productions / Warner Bros. Television

However, writers delayed our gratification and left us hanging for a few seasons. When they eventually got together, they faced a lot of insecurity, but eventually made for an amazing couple. It’s never that easy on TV though. They broke up and broke our hearts many times over. They dated other people and for awhile it looked like they would never rekindle their flame. Just as the show was wrapping up, writers threw us a curveball and brought to the two back together. This time marriage and a baby were thrown into the mix. 

24. Sex And The City – Aidan and Carrie

Today, most Sex And The City fans overlook the whole Aidan saga and tend to focus more on Carrie’s tumultuous romance with Mr. Big. However, the breakup between Aidan and Carrie was more crushing than any other in the series. While Mr. Big was obviously “the guy” on the show, Aidan was something special.

Paramount Pictures / Newsmakers / Getty Images

He never let his ego get in the way of how he felt. The man knew what he wanted, and that was to marry Carrie. Once the two decided to get hitched, we thought Sex And The City was going to change forever. Sadly, Carrie left the down-to-Earth hunk when she realized that she still had feelings for Mr. Big. Seeing a sad Aidan step into obscurity definitely left for one the saddest TV breakups. 

25. Grey’s Anatomy – Callie and Arizona

If you weren’t watching Scrubs back in the 2000s, you were likely tuning into Grey’s Anatomy. The popular hospital drama had no shortage of heartbreaking splits. Who could ever forget when Meredith and Derek broke up or when Christina and Preston called it quits? Amid all of the heartbreak, one split took the cake and that was Callie and Arizona’s acrimonious departure. 

Touchstone Television/ABC Studios

We wanted nothing more than for these two to live happily ever after and it almost seemed possible at one point. However, disagreements regarding children and career moves led to them divorcing. We particularly felt bad for Arizona, who didn’t only lose the love of her life, but also nearly lost her child in a nasty custody battle.

26. Friends – Monica and Richard

One has to question how sad this breakup really was. On one hand, we really liked Richard and his crazy mustache. However, In our hearts, us Friends fans wanted Monica to be with Chandler. We were kind of pulled between the two forces.

IMBD / Columbia Pictures Television

It sadly wasn’t destined to be. Richard was a family friend, had adult children and didn’t want anymore. These factors left for multiple strains in their relationship. What made the break up sad was that they really did love each other. He makes a few comebacks throughout the series and one point even tries to steal Monica from Chandler.

27. Frasier – Frasier and Julia Wilcox

When Frasier came to an end back in the 2000’s, fans never got the farewell we were hoping for. We wanted to see Frasier fall in love, get married and live happily ever after. However, he just moved on. He got a job in San Francisco and the book of Frasier which went as far back to the early 80s closed forever.

IMBD / Paramount Television

Amid the many women that Frasier had in his life, there was one we all thought he’d end up with for sure and that was Julia Wilcox. She was the new financial analyst at the radio station and she was immediately established as Crane’s opposite. Their squabbles immediately took fans back to the days of Sam and Diane on Cheers. They even paid homage via a line delivery. Ultimately, they did have a budding romance, but just like all women before her, Julia ended up leaving Frasier.

28. Gilmore Girls – Rory and Jess

Between the oversensitive Dean and the arrogant Logan was Jess. Jess brought balance to the men in Rory’s life. He was the tough guy with the sensitive soul. If he wasn’t reading his Allen Ginsberg poems, he was likely breaking into a car or skipping school to work at the local Walmart.

IMBD / Warner Bros. Television

We couldn’t blame the teenage Rory for getting a crush on him and kicking Dean to the curb. While Jess was cool, their time together was shaky. He just didn’t know how to treat Rory right and he eventually leaves for California. He’d return in later seasons but to the dismay of Jess fans everywhere, the two’s romance would never take off again.

29. The Office – Dwight and Angela

The relationship between Dwight and Angela was absolutely grueling at points. However, we were constantly rooting for the pair to make it. Angela who was often quiet, bitter and person of a single disapproving expression was made human by her secret relationship with Dwight.

IMBD / NBC Universal Television

At one point, they broke up and we were absolutely crushed. Then to our delight, they got back together but both cheated on each other and broke up again. Angela later fell in with Robert and had a baby with him. At this point, we were quite certain our chances of seeing her and Dwight in romantic bliss were over. In an amazing twist, the baby ended up being Dwights and then they got married.

30. Married With…. Children – Steve and Marcy

For the first three and a half seasons of Married with…. Children, Marcy D’Arcy was Marcy Rhoades. While Marcy and her second husband Jefferson were complete opposites, her and Steve were a perfect fit. He was a snooty banker who stood by his wife 100% of the time. However, time living next to the Bundy family changed him and eventually Steve began turning to Al for some male bonding.

IMBD / Columbia Pictures Television

Eventually, Steve finds that the yuppy lifestyle has lost its charm and he leaves Marcy for a job as a ranger at Yosemite National Park. Steve fans missed his presence on the show, as Jefferson would take his place as Marcy’s husband and change the dynamic significantly.

31. Happy Days – Fonzie and Ashley Pfister

It seemed like the one thing that Fonzie was never destined for was true love. Sure he played the field and impressed the ladies with his ability to change a song on the jukebox with a snap of the finger, but nothing ever lasted. Then came along Ashley Pfister on the show’s 10th season.Seeing her was love at first sight for Fonzie. Lacking details about her, he made the whole town look for her for him.

GettyImages / ABC Photo Archives

Ashley was far from typical. She was not impressed at all by Fonzie’s tough guy act and actually made him work for her love. Despite being opposite, they eventually do have a romance together. However, once the 11th season begins, fans just never hear about her again. Ashley just vanished and Fonzie was alone again.

32. California Dreams – Tiffani and Jake

Of all the Saturday morning Saved By The Bell rip offs, California Dreams was the most popular. Tiffani Smith was the show’s Kelly. She was the pretty girl with a heart of gold. She sung, she surfed was very understanding. Jake was the Zack. He was the bad boy of California Dreams. He rode a motorcycle, had good hair and took no slack from anyone. Naturally, these two would be the show’s power couple.

dream517 / Youtube

They first came together during the second season after a long build up of romantic tension. After a season bliss, problems started finding their way into the love nest. While they did break things off at the end of the second season, they’d eventually rehash things as the series was ending.

33. Grey’s Anatomy – Preston and Cristina

Grey’s Anatomy has been going strong for nearly fifteen years. There’s been many dramatic romances throughout the show’s runtime. However, none of them were as memorable as the relationship between Preston and Cristina. In the beginning, this couple really tried to keep things on the down low.

IMBD / ABC Studios

As the episodes went on, their drama became ours. Preston was quite prone to flying off the handle. He didn’t only end things with Cristina once but twice. The first breakup had to do with him wanting to protect their reputations and the second had one to do with Preston not feeling right about marrying her. In a nightmarish scenario, he left her at the altar.

34. Felicity – Felicity and Ben Covington

Talk about anticipation. When Ben Covington left a somewhat flirty note in Felicity’s yearbook, she scraped her plans for the future and followed him to New York. This wasn’t the plot to a horror flick about a stalker, rather just another charming 90s sitcom.

IMBD / Touchstone Television

To begin with, Ben is quite uncomfortable with Felicity and we can see why. However, after a couple seasons their strange friendship blooms into a romance. The whole show built up to that moment, but after a brief time as lovers, they quickly go back to being friends. Ben proves to have a slew of problems that sway him from living up to his full potential.

Sources: MSN, Today and Wikipedia