13 of the most awkward anime romances ever

Contributed by
Feb 14, 2017, 12:00 PM EST

Romeo and Juliet. Rhett and Scarlett. Jack and Rose. Sebastian and ... Grell?

Awkward is an understatement when it comes to star-crossed anime couples (or cases of crushes who don't crush back). Romance is either an alien concept or a mode of manipulation — and either achieved with saccharine sweetness or destroyed by dark magic. Homicidal maniacs lure in lovers while schoolgirls stumble over Dating 101 and romantic prospects turn even more Grim for a certain Reaper. From jellyfish love triangles to serial killer boyfriends to anti-love potions and mysterious men from the Megaverse, these twisted two-dimensional relationships are animated to be heartbreaking and hilarious.

This Valentine's Day, anime and chill with a heart-shaped mochi and fall head over high heels for these 13 awkward anime couples whose misadventures suddenly make online dating look almost desirable.

Sophie and Howl (Howl's Moving Castle)

Jealousy can be mystically cruel when magic is involved. When the Witch of the Waste thinks young milliner Sophie stands in the way of her snaring handsome enchanter Howl, she turns the unsuspecting girl into a frost-haired woman no younger than ninety. While she can't hide her age, she can mask her affection for him even as it grows more and more painful to pretend her feelings are no more than platonic. Winning over a wizard would only get that much more complicated when you've been bewitched by a spell that ages you beyond the help of even the most expensive beauty cream.

You should know who you’re dating (or in this case, wish you could date) before you move into his steampunk-ish walking castle, but between Howl’s ever-changing hair and Sophie’s mysterious morphing back into her younger self by moonlight, neither knows who the other is supposed to be. Never mind that Howl’s mysterious undertakings at night make him more of an enigma until everything unravels in the face of catastrophe. Sometimes it just takes saving a fire demon to show you love someone.


Yuri and Victor (Yuri! On Ice)

When you're an elite skater with podium-level dreams, it doesn't get much more awkward than running into the skater you idolize (and also happen to think is insanely gorgeous) stark naked in a hot tub. Except the awkwardness doesn't stop there. Just imagine your ultimate crush rising out of the seafoam — or steaming water — like Venus on the half-shell, saying he desperately wants to coach you even though you're dead last in the standings. Angels would sing.

It seems that every potentially perfect moment between Victor and Yuri is ruined by some massive misstep. They never actually kiss because something or someone always manages to sabotage the mood. Yuri is so clumsy off the ice that he pretty much curses everything he does on dry land. When he runs to embrace Victor in tears after his short program, they end up crashing to the ice in front of a sold-out stadium. Also, the last thing you want to hear is a public service announcement that you're getting married when you're not even engaged (yet). It's a wonder how that didn't put the relationship on ice.


Kuranosuke, Tsukimi and Shu (Princess Jellyfish)

Jellyfish otaku and aspiring fashion designer Tsukimi is pulled underwater into an unlikely love triangle between two gorgeous guys who just happen to be brothers. That last part is where things get complicated. Wealthy politician's son Kuranosuke thinks his chronic virgin of a brother should stay married to the government work he obsesses over, and Shu wouldn't even dream of his younger brother being halfway dateable because Kuranosuke happens to love walking the streets of Tokyo like a runway in ostentatiously fancy (and obviously expensive) women's clothes to skirt potential political obligations.

Tsukimi first found herself ensnared in the tentacles of love when she tried to rescue a jellyfish from a pet store and a supposedly female stranger came to the misunderstood invertebrate's rescue. Who she thought was, as the self-proclaimed unfashionable geek puts it, an enviably "fashionable lady" turned out to be the most beautiful boy she'd ever seen sans wig and makeup. Bonus: Tsukimi turns to stone (as in actually turns into a granite statue on screen) if she's embarrassed in front of either brother. She literally looks like she just saw Medusa.


Inari and Shu (Princess Jellyfish)

Shu, despite having zero experience in anything remotely related to romance, suddenly finds himself entangled in not one but two love triangles. His daydream fantasies all center on the mysterious jellyfish girl who can undergo a Cinderella transformation from sweats to couture dresses as if by magic (thanks to Kuranosuke). Unfortunately, being mired in politics means he has to deal with unsavory characters like Inari.

The only involvement Shu has or wants with Inari is government business, but he's not exactly convinced the Amamizu-kan complex (where Tsukimi lives with her otaku roommates) should be torn down as she proposes. So what do you do when you're a selfie-addicted seductress bent on getting her way? You lure him into your apartment, spike his drink with sedatives so he won't remember what he did (or didn't do) in the morning, rip his clothes off, shove him into bed and take an incriminating shot that you then proceed to smear all over social media. Then you keep giving him post-meeting reminders that you did reprehensible things forever immortalized on the internet. That's one way to close a deal.


Ponyo and Sosuke (Ponyo)

Not to hate on interspecies dating, but it doesn't get much weirder than falling in love with a goldfish — even if she's really a hybrid of human and goldfish genes that came out of the union of a mad sorcerer and a mermaid (don't ask). It gets even weirder when said goldfish-girl sprouts limbs and washes up onto the shore to walk right next to human crush Sosuke. She could be walking next to him in human form one moment and then devolve into something fishier when it rains. Not that he seems to mind.

This relationship redefines the Facebook concept of "it's complicated." There is a reason Ponyo's father was so overprotective he imprisoned her — and her hundred or so sisters that spawned from his own strange love affair — in a bubble. If being involved with someone of another species provokes a massive shift in tidal forces, get your galoshes out and prepare for floods so massive that what were once roads are now rivers swimming with sea creatures. You must be serious about someone if dating them means disrupting the natural order.


Lizzie and Ciel (Black Butler)

Snobbish 13-year-old earl Ciel Phantomhive is stifled by Lizzie's over-the-top efforts to be ridiculously cute for him in every humanly possibly way. She's all frilly dresses and flowers and hair ribbons while he remains the somber Gothic aristocrat. Though Ciel despises his birthday because it memorializes the murder of his parents, Lizzie insists on cheering him up by throwing the reluctant earl an uber-kawaii party sugared over with stuffed animals and so much pink it could give anyone a toothache before ever taking a bite of cake.

Even candy isn't always sweet (and sometimes there might be a bitter secret hidden in the middle). What Lizzie is keeping from her significant other is that she wishes to stay eternally saccharine so he can protect her. When Ciel runs into an army of undead that almost claim him for a corpse, she transforms into a fierce pigtailed fencer who doesn't let lace undergarments get in the way of slaughtering zombies.


Grell and Sebastian (Black Butler)

Irreconcilable differences aren't enough to stop some people from going after the object of their affection. The fact that Grell is a Shinigami (Grim Reaper) who reaps souls with a chainsaw and Sebastian is a demon who devours them never deterred his undying crush on the barely amused butler. He also clearly has no manners — another thing that Sebastian, as a butler, finds abhorrent. Grell is always butting into situations, even when he's suspended and all he can use for a death scythe against a horde of creepy dolls is nothing but a pair of scissors. He'll go up against them in the name of unrequited love even when Sebastian's unnatural strength is enough to face an army of murderous mannequins.

Grell’s cringe-worthy pet names “Sebastian Darling” and “Bassie” in the English version are ridiculous enough, but not quite as flagrantly offensive as what he calls his beloved butler in the Japanese version, warping his sophisticated name to “Sebas-chan.”  You shouldn’t be calling anyone, let alone the butler to the Queen’s royal watchdog, anything “-chan” unless the person in question is extremely close to you or under twelve. 


Naru and Nephrite (Sailor Moon)

While any other romantic trials in Sailor Moon are often overshadowed by Usagi's quest to win the heart and top hat of the infamous Tuxedo Mask, there is one deranged romance early on in the series that is supernaturally disturbing. Never mind the supposed age difference being vastly inappropriate (though a nearly immortal minion of Queen Beryl must be hundreds or even thousands of years older than he lets on). Nephrite's manipulative powers send Naru hurtling head-first into the chasm of evil after he assumes an alter ego as playboy millionaire Maxfield Stanton. When you're 15, it's easy to believe in fantasies you've been brainwashed into by the henchman of an evil space queen.

Maybe the most surprising thing of all in this twisted tale of star-crossed lovers is that Naru's affection for Nephrite turns genuine even after the manipulation curse is no more. Not that she has any business with a sorcerer from some galactic otherworld. When he turns on the Megaverse, she defends him and joins him on the quest to stop evil — but not before Beryl gets revenge and he disintegrates into dust.


Sailor Moon and Tuxedo Mask (Sailor Moon)

There can't possibly be an awkward anime list in the universe that doesn't include the unlikely magical girl and her knight in black and white, because the only place this romance is actually perfect is in Usagi's imagination. She doesn't even suspect her human-world nemesis Mamoru of being the man of her dreams who only materializes after she's morphed into Sailor Moon. Usagi can't stand Mamoru in real life, and the feeling seems to be mutual. She ironically enough could be standing right next to him while fantasizing about the dreamy Tuxedo Mask she meets on her Megaverse-crushing adventures.

It isn't like Mamoru is in tune with reality either. He has trouble demystifying what his recurring dreams whisper to him about the mysterious masked man he transforms into in the alt-verse, and he always keeps wondering about the girl with twin tails who seems strangely familiar. Never for a moment does he pause to put that and "Meatball head" together into an equation that equals Sailor Moon. Love may be blind, but in this case wearing a mask you never take off is blinding.


Kaede and Nagisa (Assassination Classroom)

While would-be assassin Kaede isn't shy Nagisa's target from the first day of class, it might be for the better since they are always competing against each other to annihilate Koro Sensei, a human mutated by government experiments into a yellow tentacled creature that flies at warp speed and has a perpetual grin plastered on his face. Somehow they and their classmates have to go through with this assassination operation before he destroys the Earth as promised. Kaede's outspoken self-consciousness about her cup size (or the lack thereof) isn't the best way to get attention, but you can hardly blame a teenage girl whose teacher is literally a perverted octopus. Nagisa is is just romantically inept. Nothing against boys with blue hair.

The uneasy undercurrent of romance between these killers-in-training is left in the shadows with the potentially lethal secrets they keep from each other. Neither makes a move too soon — too much assassination training could be subconsciously influencing them — but they unfortunately wait until it's too late. Their first (and only) kiss happens unexpectedly in the middle of a federal crackdown on Koro Sensei. How romantic.


Irina and Karasuma (Assassination Classroom)

If adolescent assassins dating each other isn't awkward enough, try career assassins disguised as teachers who are laser-focused on eradicating the huge yellow smiley-face version of Cthulhu otherwise known as Koro Sensei. Irina is simultaneously trying to kill Karasuma's ignorance and snare his attention with ill-timed flowers and uncomfortably tight button-down blouses. Even her gym class attire looks more like lingerie. The fact that these weapons of mass seduction are aimed at just one man doesn't deter the boys (and Koro Sensei) from giving her a bit too much attention.

Karasuma is already married — to his work. His love affair with the Japanese government's undercover division runs too deep for him to be diverted by anything as frivolous as love letters or chocolates in heart-shaped boxes. He is so utterly clueless to Irina's arsenal of temptation tactics that he even gets offended when she brings him a birthday bouquet bigger than his head. Their students even set them up on a dinner date only for Karasuma to miss every remotely romantic signal from across the table. He seems more interested in the steak. And assassination.


Misa and Light (Death Note)

How anyone, even a glamorous model-actress, can stay engaged to a serial killer without being in a permanently obsessive state of paranoia is beyond human reasoning. Manipulation (and a rogue Shinigami who thinks the human world is one hilarious reality show) is the foundation of this sham relationship that homicidal genius Light aka killing machine Kira is only using to his advantage as he keeps sending victim after victim to the grave. Not that she started out innocent: Misa only met Light after she stared experimenting with a notebook from the underworld that will automatically kill the person whose name is written inside.

Misa's ignorance to Light’s machinations is so obvious it's disturbing. Her psychopath fiancée is out murdering people one after another and she's prancing around in kitten heels and lace lingerie in a heated debate with herself about how to impress him. Any sane person would have taken Light's coldness and constant ignoring of her frilly, lacy come-ons and used it as an excuse to throw her engagement ring in his killer notebook and run before he can write her name in there.


Ichigo and Orihime (Bleach)

Orihime may be stalked by at least half the boys and a handful of girls at school, but the parade of adolescent hormones is invisible to her since she only has eyes for angst-ridden Ichigo. An early run-in with him prompts her to rattle off her bizarre grocery list. Ichigo may be brave enough to destroy demon monsters that feast on human souls, but no one can blame him for not wanting to undertake a taste test of whatever this girl has in mind to make for dinner.

As if Ichigo's lack of emotion doesn't already freeze the situation over, his inability to control Kon (a scraggly teddy bear possessed by a defective soul) from bouncing around and sticking his face into Orihime's cleavage doesn't exactly break the ice. Her would-be boyfriend is always so grouchy because he's exhausted from being a part-time Shinigami fighting ghost battles in the beyond. She only gets his attention by saving his life in one of bloody clashes — because being rescued from the brink of death is the only surefire way to wake up someone so oblivious. Love is a battlefield.