Not all couples can be as epic, endearing, or believable as Ricky and Lucy, Homer and Marge, Buffy and Angel, or even Will and Grace. There are plenty of TV couples that should not have happened, romantic pairings that left viewers with more of a head-scratching "what?" than a heart-melting "aww." Call it an attempt at something different, a venture towards a new kind of chemistry, or even a joke - however you slice it, these are TV characters who shouldn't have gotten together.
The good news is that all of the characters here were on successful TV series that more or less survived their ridiculous coupledom. None of the shows went down the tubes because of a romantic mismatch. In fact, in a few notable cases, the coupling of these unlikely twosomes became the focal point of the entire series (hi, Ross and Rachel).
Like Ann Perkins on Parks and Rec, Jackie dated most of the major male cast members of That '70s Show at one point or another. Mercifully, her relationship with Fez was the most short-lived of them all. Nothing about these two together made any logical sense, at least to most fans.
Jackie had a naturally abrasive personality, and at least in the earlier part of the series, she looked down on Fez. And Fez, despite his dimwittedness, was good-natured and kind. After she dismissed him for so long, it stretched the bounds of credulity that he would suddenly want a relationship with her once she did an about-face.
Willow and Tara were exactly the witchy lesbian power couple the world needed. So, after Tara's passing, there were big shoes to fill - and slayer Kennedy was not the one to fill them. In contrast to Tara's sweetness, gentleness, and good humor, Kennedy was pushy, privileged, and a tad arrogant.
Viewers were confused as to why Willow would ever be interested in her, especially so soon after Tara's demise. But, alas, Kennedy stayed on - meaning, she lived - through the finale and into the subsequent comic book series.
Let's face it: As lovable and fabulous as Ann Perkins was, she was hopeless with relationships for most of her time on the show. At one point or another, she dated half the men in Pawnee and almost all of the major male characters on Parks and Rec. Given those odds, a few mismatches were bound to occur, and her short-lived relationship with Tom Haverford was the most unbelievable of them all.
Tom was a total frat bro, obsessed with money, status, and things. Yes, he was cute and charming in his constant, mostly failed quest towards materialistic perfection, but he and Ann simply didn't go together. By contrast, she was a sweet-natured, big-hearted nurse with a modest home and dreams. She deserved so much better than Tom. Thank Li'l Sebastian that Chris Traeger came along when he did.
Much to the surprise of many viewers, Callie and George started dating during Season 2 of Grey's Anatomy. Even more surprising, during Season 3, they ran off to Vegas for a quick wedding. Though these two characters were likable, they were a strange pairing from the beginning, considering the connection George had with Izzie.
Ultimately, it was a dalliance with Izzie that led to George's eventual divorce from Callie. Later, Callie began to date women, and George got hit by a bus.