Top 10 Failed Romances That Were Actually Perfect Pairings

To All the Boys: P.S. I Still Love You (2020)

This romantic comedy sequel film picks up where the first left off, with Lara Jean in an official relationship with her longtime crush Peter. When John Ambrose, another recipient of Lara Jeans past love letters, comes into the picture, it sparks a love triangle between Lara Jean and the two boys. Although we were rooting for Peter in the first film, John Ambrose just seemed like a better match for Lara Jean. They had much better chemistry, far more in common, and Jordan Fisher is obviously too cute to turn down. As a result, fans are divided over this films ending, which sees Lara Jean and Peter once again reaffirming their feelings for each other.

Sky High (2005)

Hippie plant-lover Layla Williams seemed like a perfect match for the 2000s emo dream troubled teen Warren Peace, and their chemistry in the Chinese restaurant scene was off the charts. Instead of letting Layla end up with her perfect match, this film took the cliche route of having her best friend and protagonist Will Stronghold realize she really was the one for him all along. After ignoring his friends for the entire movie, is that really the ending Will deserved? Its certainly not what Layla deserved, despite the movies insistence that she was crushing on Will and not Warren. This outcome completely scrapped all of Laylas character development in favor of giving Will a happy ending.

The Marvelous Mrs. Maisel (2017-23)

This Amazon Prime series pairs its fictional protagonist, aspiring comedian Midge Maisel, with real life counterculture comedian Lenny Bruce, and sparks fly. The two are equally matched in wit and charisma, with incredible chemistry from their very first scene. Unfortunately, this relationship was doomed from the start due to the real life Lenny Bruces untimely death in 1966 at just forty years old. This made the unbelievably romantic scenes these two characters shared completely heartbreaking. No matter how much fans desperately wanted Midge and Lenny to get their happy ending, it was tragically never meant to be.

Pitch Perfect (2012)

The first suggestion that something might happen between these two a cappella singers comes early in the first Pitch Perfect film. Chloe barges in on Becas shower to urge her to join the Barden Bellas after hearing her sing. This highly suggestive scene was just the beginning of many flirtatious moments between these two characters that led to some serious queerbaiting accusations from fans. The possibility of a relationship between Beca and Chloe was hinted at in marketing for the films sequels, but they ultimately ended the series as strictly friends. For LGBTQ fans watching with the hope of seeing their community represented in a major Hollywood franchise, this was totally disappointing.

That 70s Show (1998-2006)

The two characters with the biggest personalities on this series seemed like an unlikely pairing, but quickly became a fan favorite couple after they initially got together. After Kelsos horrible treatment of Jackie during their relationship, it was refreshing to see Jackie and Hyde treating each other with respect and admiration. Their differences as people made for a relationship where both parties were constantly growing and improving themselves to be better partners to each other. Jackie ends the series paired with Fez but is revealed to be married to Kelso in the reboot That 90s Show. This upset fans, who rightfully asserted that Jackie deserved better than to end up with someone who treated her so poorly.

Modern Family (2009-20)

Fans of this long-running sitcom watched the eldest Dunphy fall in love and have her heart broken multiple times throughout the shows eleven seasons. By far, the most popular boyfriend Haley ever dated was male nanny Andy, played by Adam DeVine. While Haley and her previous long-term boyfriend Dylan clearly had strong feelings for each other, Haley and Andy had what seemed like a much healthier dynamic. They supported each others dreams and truly wanted the best for each other, which led to Haley encouraging Andy to take a job opportunity in another state. It was a selfless action that cost this couple their happy ending, but showed how much Haley had grown as a person throughout her relationship with Andy.

Gilmore Girls (2000-07)

This relationship truly was meant to be endgame, but off-screen complications ruined what could have been for poor Lane Kim and Dave Rygalski. These characters shared a mutual passion for music and each other, despite Lanes strict mother making dating a near impossibility. Dave went above and beyond to prove to Mrs. Kim that he would be a suitable boyfriend for her daughter. Sadly, Dave was swiftly written out of the show when the characters actor, Adam Brody, was cast on The O.C. This was clearly not what the writers wanted for Dave, which is proven by his name alone. The character Lane Kim is based on Gilmore Girls writer and producer Helen Pai. Her real-life husbands name? David Rygalski.

Fleabag (2016-19)

This brilliantly written British series confronted religious taboos when it introduced a Catholic priest as the main characters love interest in season two. For the first time, this misunderstood, misguided, hot mess of a character meets someone who matches her wit and truly sees her, and hes completely off limits. Their palpable chemistry keeps viewers on the edge of their seat all season, waiting to see if the Priest will ultimately sacrifice his career for the woman hes come to love. In the end, the Priest chooses God over Fleabag and the two part ways in one of the most heartbreakingly real scenes in recent television.

Supernatural (2005-20)

One of the defining moments of 2020 was, without a doubt, the final season of Supernatural. For years, dedicated fans of this series advocated for writers to pair up Dean Winchester and the angel Castiel, but their pleas were ignored. Fans were forced to create copious amounts of fan fiction and art themselves, never imagining the showrunners would ever make the ship officially canon. Much to the surprise of viewers, one of the shows final episodes saw Castiel actually confessing his love for Dean. Of course, he was immediately banished to the Empty, which fans refer to as Superhell. This was hardly the ending Destiel fans wanted, and felt so unnecessarily tragic after years of hoping for a romantic confession between these fan favorite characters.

Casablanca (1942)

In one of the most iconic love triangles in the history of film, Casablanca tells the complicated story of Rick Blaine, his lost love Ilsa, and her husband Victor. Ilsa needs Ricks help in order for her and her husband to escape Nazi officials, but she also reveals that her feelings for Rick have never faded. This classic film combines political tension with romantic tension that leaves you wondering throughout whether Rick and Ilsa will end up together. Ricks love for Ilsa means he must ultimately act selflessly to help her and her husband safely escape. Its clear Ilsa loves both Rick and Victor, and it was only a matter of circumstances that led to her choosing her husband over her former lover.

Do you think these couples were meant to be, or did they get the ending they deserved? Let us know in the comments!