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VOICE OVER: Phoebe de Jeu WRITTEN BY: Taryn Crankshaw
We all know these TV characters who should have ended up together. Our countdown includes "The Office," "Community," "Gossip Girl," and more!

#20: Alex Karev & Jo Wilson “Grey’s Anatomy” (2005-)

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At the hospital formerly known as Seattle Grace, broken hearts are plentiful. In one of the most soul-crushing storylines, surgeons Alex Karev and Jo Wilson meet, fall in love, break up and go through lots of drama before eventually saying “I do”. However, their marriage comes to a screeching halt when Alex learns that he’s the father of his ex, Izzie’s two children. To make matters worse, he shares the news with his wife via a letter. Ouch. Despite the explosive reveal, the couple had a lot of untapped potential. Unfortunately, this is one case of love gone wrong that not even the most talented Anatomy surgeon can piece back together.

#19: Andy Bernard & Erin Hannon “The Office” (2005-13)

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After The Office’s favourite couple Jim and Pam finally get together, the series finds its next big romance in none other than Andy and Erin. The acapella singing salesman and bubbly receptionist start dating in season 6, but end shortly after and Erin starts to date Gabe. It’s clear that they still have strong feelings for one another, and they reunite in season 8 but break up again after Andy leaves her behind to sail off to The Caribbean. Erin finds comfort in season 9 addition Pete Miller, which is the final nail in their on again off again romance. Perhaps, these two aren’t meant to be endgame, but given all the hoops they have to jump through to finally be together, it would have been nice to see where their relationship could have gone.

#18: James "Sawyer" Ford & Kate Austen “Lost” (2004-10)

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Yes, Lost is chock-full of bizarre mysteries (Hello, Smoke Monster!). But one thing that doesn’t need any explanation is Sawyer and Kate’s off-the-charts chemistry. Referred to by fans as “Skate”, the pair bond over their criminal pasts and similar personalities. However, their other respective love interests, Jack and Juliet, get in the way of anything ever taking flight. Sadly, viewers never get the opportunity to see their relationship truly flourish. Maybe in some parallel universe, these kindred spirits finally got their justice and by Lost standards...that's definitely a possibility.

#17: Special Agent Dale Cooper & Audrey Horne “Twin Peaks” (1990-91)

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David Lynch’s seminal TV series about a murder in small town America didn’t fare well during its initial release, but has since developed a cult following. So much so, the show was revived in 2017. One of the pillars of the original series was the relationship between FBI agent Dale Cooper and eighteen-year-old Audrey. While the two were never officially a couple, you’d be hard pressed to argue against their obvious chemistry. Ironically, the two were supposed to end up together, but Kyle MacLachlan vetoed the idea, claiming Cooper would never date a teenager. Too bad, these two would have made one hell of a duo!

#16: Hayley Marshall-Kenner & Elijah Mikaelson “The Originals” (2013-18)

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When it comes to vampire-themed romances, these two take a bite out of the competition. In The Vampire Diaries spin-off, their passion and deep-rooted feelings for each other seem eternal until season 5, when Hayley attempts to save Klaus and Hope by giving up her own life. What makes their story even sadder is that Elijah, who suffers memory loss at the time of her death, eventually regains his memories and has to come to terms with losing the love of his life. Their story has all the features of a Greek tragedy, including a gut-wrenching ending that still has fans reaching for the tissues years later.

#15: Samantha Jones & Smith Jerrod “Sex and the City” (1998-2004)

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It’s hard not to wonder what could have happened if Carrie and Aidan worked out, but the real couple that City fans can’t get over is Samantha and Smith Jerrod. When the budding actor appears in season 6, he convinces Samantha that their connection is more than just a fling and thus begins her first real committed relationship. On the outside, they’re picture-perfect, but on the inside, they endure many challenges, including her breast cancer diagnosis. In the 2008 Sex and the City movie, she breaks it off with her celebrity beau after realizing that she’s lost part of herself. Samantha is meant to be single and independent, but fans also love the power couple and can’t help but tear up over their bittersweet breakup.

#14: Clark Kent & Lana Lang “Smallville” (2001-11)

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On the surface, dating a superhero looks like fun, but if Smallville taught viewers anything, it’s that defending the universe comes with plenty of baggage. When the series introduces us to teenage Clark Kent and his peer, Lana, it’s clear that they will become more than friends. Referred to by fans as “Clana”, the couple battle bad guys, secrets and heartbreak. Despite all that, Clark’s aversion to kryptonite is what ultimately tears the couple apart and they go their separate ways, but always long for each other. And sure, it’s true that Lois Lane and Clark Kent are soulmates, but it’s still nice to think about what could have transpired if these high school sweethearts had ended up together.

#13: Buffy Summers & Spike “Buffy the Vampire Slayer” (1996-2003)

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These two take the word frenemies to a whole other level. After arriving in Sunnydale, Spike, a deadly vampire, finds himself falling for his arch-nemesis, vampire slayer extraordinaire, Buffy Summers. Within time, genuine love and affection develop between the two and kick starts a passionate romance. Spike even goes as far as to regain his soul to prove his love for her. However, in the series finale, Spike perishes after sacrificing himself. Although it’s done for the greater good, the fact that these two don’t end up together drives a stake through all of our hearts.

#12: Phoebe Halliwell & Cole Turner “Charmed” (1998-2006)

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Being half-human and half-demon is definitely a relationship killer. In season 3 of the supernatural drama Charmed, witch Phoebe and Cole Turner end up falling for each other and ignite a romance of epic proportions. Facing myriad challenges, including demonic possession, the pair struggle to obtain any sense of normalcy in their marriage and things fall apart when Cole becomes The Source of All Evil. Yikes! Phoebe does move on and finds love again in a cupid named Coop, but there’s no denying that her relationship with Cole was nothing short of magic.

#11: Haley Dunphy & Andy Bailey “Modern Family” (2009-20)

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Seriously, we couldn’t name a cuter couple than Hayley and Andy. They are the textbook definition of the word and made our hearts swoon whenever they’re on screen. After scoring his dream gig as a real estate agent in Utah, the former nanny and Phil and Claire’s eldest child make the difficult choice to end their relationship, breaking viewers' hearts in the process. Fans were always hoping that down the line the two would reunite, but they both end up moving on. Although fans will always have a soft spot for Dylan, it’s hard not to miss Andy. Yes, it's a shame that they weren’t endgame, but it’s nice to know they both got their happy endings… even if they’re not with each other.

#10: Nick Andopolis & Lindsay Weir “Freaks and Geeks” (1999-2000)

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While there are some who will claim that Lindsay would have ended up with Daniel had “Freaks and Geeks” been renewed for a second season, we are firmly entrenched in camp Nick. A total sweetheart played by a very young Jason Segel… what’s not to like? Sure his advances might have been a little over the top, but Lindsay was his first love. And honestly, who didn’t make a fool of themselves in high school? It’s a shame this couple wasn’t given more time to move forward on their relationship, but alas, it wasn’t meant to be. Or the show got canceled. Either way, it’s a total bummer Lindsay and Nick couldn’t make it work.

#9: Jeff Winger & Britta Perry “Community” (2009-15)

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How these two didn’t end up together we’ll never know. From the very first episode of “Community,” it was made abundantly clear that Jeff had the hots for Britta; that is, until he started to see Annie in a new light. The show’s first season ended in a three-way “will they won’t they scenario” between the characters, with Jeff ultimately choosing Annie. However, in a show as layered as this one, that relationship didn’t exactly go off without a hitch. It’s a shame Jeff and Britta never made it work, as they really are cut from the same cloth.

#8: Jackson Avery & April Kepner “Grey’s Anatomy” (2005-)

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Over 17 seasons, Grey’s Anatomy has had some memorable couples and high on that list are Jackson and April. Who could forget when he crashed her wedding and professed his love? Afterwards, they seemingly run off into the sunset. But of course, this is Grey’s we’re talking about and their bliss is short-lived. They battle over religious beliefs and deployment and survive the tragic loss of their child, Samuel. They end up divorcing, but not before April becomes pregnant. In May 2021, it was announced that actor Jesse Williams would leave the series after season 17. Meanwhile, during that same season, Jackson, April - who’s no longer with her husband Matthew - decide to move to Boston with their daughter. So, perhaps, there is still hope that the Seattle Grace alumni will get their happy ending.

#7: Freddie Benson & Carly Shay “iCarly” (2007-12)

“iCarly” is about three teenage friends whose web show becomes an overnight sensation. Starring Miranda Cosgrove and Nathan Kress as Carly and Freddie, the show touched upon their feelings for one another numerous times throughout its multiple season run. In fact, the characters did briefly date after Freddie saved Carly from getting hit by a taco truck. Carly later tells Freddie she loves him, but nothing comes of it, as Freddie is worried that she is only into him because he saved her. While the sitcom teases a relationship between the characters in the final episode, even going so far as to show them kissing, it remains unclear whether or not they ended up together.

#6: Shawn Hunter & Angela Moore “Boy Meets World” (1993-2000)

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Poor Shawn. For seven seasons, he served as Cory’s best friend and confidant, and together they navigated the troubled waters of being a teenager. While Shawn has plenty of girlfriends throughout the show’s run, he envies the fact that Cory and Topanga are in a loving, long-term relationship. Enter Angela. Introduced in season five, she would prove to be Shawn’s primary love interest for the better part of two seasons. The two had much in common, including the unfortunate fact that both came from broken homes. Sadly, this plays into why Angela ultimately breaks things off with him, claiming she’s scared that she will inevitably hurt him. Cue the waterworks.

#5: Jess Mariano & Rory Gilmore “Gilmore Girls” (2000-07)

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These two lovebirds are pure early 2000s nostalgia. Bonding over their shared love of books and music, the two teens start to date and melt a few hearts in the process. Although they’re total opposites, they challenge each other. Rory cuts through Jess’s tough persona and he supports her ambitions as a journalist. Sadly, the stars aren’t aligned for the pair and they break up for good when Jess abruptly leaves town without notice. The two are on good terms in the 2016 sequel Gilmore Girls: A Year in The Life, but sadly do not revisit their romance. Here’s hoping that if fans ever get another follow-up to the series, that they rekindle what once was.

#4: Jackie Burkhart & Steven Hyde “That 70’s Show” (1998-2006)

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These total opposites work so well together, it’s hard to remember that at one time they couldn’t stand each other. Throughout her tumultuous relationship with Kelso, Jackie surprisingly found a confidant in Hyde and there were even instances when he would try to convince the pair to break up. They went from frenemies to partners and created some of the series’ most adorable moments. However, like all good things, their romance comes to an end. Hyde spends some time in Las Vegas, marries someone else, then splits up with her, while Jackie ends up with Fez. It’s not exactly how fans wanted the series to end, but there’s always hope that somewhere down the line they find their way back to each other.

#3: Nate Archibald & Serena van der Woodsen “Gossip Girl” (2007-12)

Talk about a tumultuous relationship! The union between these two had more twists and turns than a roller coaster! Nate and Serena would forever be linked after it was revealed that she took his virginity prior to the events of the show’s first season. While they would remain friends for much of the teen drama – not to mention the fact that they hooked up on a semi-regular basis – they didn’t exactly stand the test of time. And while Serena lands a solid catch in Dan, one can’t help but wonder what a marriage between Nate and Serena would have been like. We’re thinking it would have been pretty hot.

#2: Barney Stinson & Robin Scherbatsky “How I Met Your Mother” (2005-14)

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From the very first episode “How I Met You Mother” made it clear that Robin and Ted would not end up together; and honestly, we couldn’t have been happier. The two simply weren’t right for each other. But you know who were: Robin and Barney. While they may have started off heading in different directions, their love for one another made everything else in their lives pale in comparison. Sure they were a little offbeat, but all the best couples are. Just look at how crazy Marshall and Lily were! But no, they had to get divorced. Seeing as how the final season is one giant lead-up to their wedding, this one was a major letdown.

#1: Klaus Mikaelson & Caroline Forbes “The Vampire Diaries” (2009-17)

Finding a single vampire these days can be tough. But you don’t have to tell these two characters that! Okay, so we get that Klaus is a ruthless killer, but that doesn’t mean he deserves to be alone. While it’s rare to see him display any positive emotions, he occasionally does so in the presence of Caroline, the object of his affection. While the two share a number of tender moments together, including a one-night stand, their relationship never amounts to anything substantial. Which “sucks,” because they would have made one sexy couple!