Most romance media, including romance anime, are afraid to crush the fragile hearts of their viewers. That's why most of them have happy endings where the protagonist usually ends up with the promised love or the next best thing. It's not for everyone, and that's okay.
Some viewers might simply crave the heartbreak they never had, among other reasons for seeking romance anime with sad endings. Failed relationships in anime, after all, are an important part of the maturing process— even for anime protagonists; besides, it can't always be rainbows and butterflies, for they only appear after the rain.
8 Your Lie In April - Two Prodigies Had Their Music Cut Short
Among the chief reasons for a lot of failed relationships in a lot of shows and films. But not many of them have come close to the soul-crushing grieving process of Arima Kosei. Because after losing his mother, he eventually found out that he was also about to lose someone else who was important to him, namely Kaori Miyazono.
Both of them were musical prodigies and Kaori became Arima's pillar of support, propping him back up after his depressive streak due to his mother's death. In this case, it would appear that Kaori was going for the manic-pixie dreamgirl trope; but she quickly subverts it by doing something that would have made the protagonist even more depressed if he had been a regular person.
7 Nana - Twice The Nana, Double The Depression
Nana is quite a handful of heavy emotions as it explores the big dreams of a province girl named Nana who moved into the city and gets involved with another girl named Nana. The second Nana belonged to a band and quickly became friends with the first provincial and innocent Nana, where the latter was dragged from one turbulent relationship to another.
What makes Nana's ending and romance so sad or disappointing was that the anime was cut short, and it just ended rather inconclusively. That's because the original manga author was battling with an illness at the time and their work went on a hiatus. So instead of getting a happy ending, viewers were mostly left with a realistic and harsh perspective on adult life.
6 School Days - A Gruesome End To Womanizing
To say that the romance in School Days ended sadly is an understatement. Because apart from the failed relationship. People involved in this anime's chaotic romance also got hurt in ways that a regular high schooler shouldn't be experiencing. Someone literally died after they broke someone else's heart repeatedly.
Cheating was involved, but one usually doesn't expect some high school students to murder another in a fit of vengeful rage out of immature love. So it's not just a bitter end to a romance that deserves it, but also a rather traumatic lesson on why one should never cheat.
5 Plastic Memories - Loving A Robot On Borrowed Time
Plastic Memories is a Blade Runner-esque story involving a human named Tsukasa and an android named Isla. Isla is an enforcer tasked with hunting down other androids who are past their expiration date of around nine years, with the help of her new partner, which is Tsukasa.
But eventually, Isla would have become the very android she used to hunt since she was not exempt from the said expiration date. The problem was, Tsukasa finds Isla beautiful, and even wanted to pursue a relationship with her. And while the ending is not entirely unexpected, it's still a regretful conclusion to a rather unique romance.
4 Psycho-Pass - Just Kiss Already!
Apart from its riveting and exciting futuristic cyberpunk crime story, Psycho-Pass is also famous for its slow-burn treatment of the two most popular protagonists, Akane and Kogami. This detective duo had been hinting at a potential romance ever since the first episode, but sadly it never blossomed into anything. Both of them were too busy.
And Kogami going rogue and becoming a fully-fledged criminal himself didn't help matters. There was a conclusive film that had every opportunity to fire up whatever vague spark of romance they had left, but duty and their ideals sadly took precedence over what could have been.
Technically, the viewers and fans didn't have a right to feel down over a romance that never was, but all that slow romantic buildup and unique chemistry for nothing— not even a kiss or something casual, was quite upsetting.
3 The Wind Rises - A Love That Didn't Survive The War
This anti-war film from Ghibli hits harder than others as it destroys romance in addition to the prejudiced and immature impressions about war. It follows the tale of an aircraft engineer and designer named Jiro who spent more time on his craft than in taking care of his ailing wife in order to fuel Imperial Japan's war effort back in World War 2.
In the end, Jiro's wife died without having seen the fruition of Jiro's ambition; Jiro also never witnessed the success of his aircraft in the war since Imperial Japan lost despite their efforts. In the end, Jiro loses friends, family, his wife, and his art due to the war.
2 5 Centimeters Per Second - Drifting Apart, Step-By-Step
5 Centimeters Per Second is based on the speed at which cherry blossom petals fall off the ground, symbolizing how humans often drift apart from one another. Thus, the anime short explores this notion through a man named Takaki Tono who, despite growing apart from her first love, was still unable to move on.
This caused Takaki's relationships to fizzle and fail. Takaki did get a chance to finally catch up to her first love, but he later realized that what he sought the most was nothing but a memory; the person he once loved no longer existed in the present. The ending was left a bit ambiguous, but it was hinted that Takaki finally learned how to move on, which is certainly bittersweet.
1 I Want To Eat Your Pancreas - More Like, "I Want To Stomp Your Heart"
I Want to Eat Your Pancreas is an even more crushing take on the dying manic-pixie dreamgirl trope which Your Lie In April masterfully told. This time around, the girl, Sakura has a fatal pancreatic illness (hence the title) and her classmate, named Haruki was the only one who found out.
The two ended up spending time together and even forming an intense and close romantic tie, partly due to Sakura's limited time. But the universe can be cruel and what ended their relationship was something rather nihilistic and even more painful than a pancreatic disease.