In the very first episode of this long running shonen series, an unpopular and unlucky middle school student named Tsuna gets the surprise of his life. A tiny hitman named Reborn shows up and forces him to train to be the successor of an infamous mafia family named the Vongola. To give Tsuna enough power to fight, Reborn shoots him with a “dying will” bullet – which causes the victim to tear off their clothes, have a constantly burning flame on their forehead, and violently carry out the last thing they regretted never doing before they were shot.

Tsuna has a crush on a cute girl named Kyoko in his class, but has never had the confidence to confess to her. But when Reborn shoots him with the dying will bullet, he turns into a raging underwear-clad maniac who sprints over to Kyoko and shouts at her to go out with him. Luckily, she’s a sweetheart and just thinks it’s a joke, but Tsuna got off to a pretty awkward start there. Maybe that’s why many fans prefer him in a yaoi pairing where he doesn’t embarrass himself...

It’s fairly common for an isekai anime to star a single man with a sizeable female harem all fighting over him, but in a show like Re:Zero, you know this mess of love triangles won’t get resolved with just some wacky hijinks. Someone’s heart is going to get seriously trampled. Sadly, this fate falls to Rem, the cute maid who confessed her love to protagonist Subaru and got shot down within moments of bearing her deepest feelings to her crush. Subaru tells her that he’s sorry, but his heart belongs to another girl named Emilia. And since Rem can’t possibly measure up to Emilia, she essentially has no chance of being with Subaru at all.

Instead of accepting this outcome, Rem devotes herself even harder to Subaru and declares that she’s fine with being just his mistress or servant as long as she can be with him. Hey Rem, have some respect for yourself! If the man you love doesn’t love you back, who needs him? You’re a great catch just the way you are and don’t need to degrade yourself for someone who will never return your feelings! ...Sorry, we’re just really emotional about this.

Yuno is well known as one of the most terrifying yandere characters in anime, and for good reason. When she’s chosen to be a player in a supernatural kill-or-be-killed battle royale, she adapts remarkably quickly to exterminating her fellow man. The only player she doesn’t view with murderous contempt is the protagonist Yuki, and that’s because she’s madly in love with him. He reluctantly teams up with her as a survival strategy without knowing why she loves him, but when he finally finds out the real reason, it chills him to his core.

One year before the main story, Yuki and Yuno were in class, filling out a form about what they wanted for their future. Yuki made a joke that the two of them could get married, and Yuno latched onto that with white-knuckle intensity. She had just done something unthinkable earlier that day and needed another person to live for, so she essentially chose him at random. And now he’s stuck with this girl forever because she gaslighted him into depending on her, too. The poor guy may never know what real love is like, and it’s all Yuno’s fault.

Are Kumiko and Reina a couple? It’s honestly pretty hard to tell. But what’s crystal clear is that they care deeply for each other, and Kumiko’s confession from episode 11 of the first season shows this in a suitably awkward way. Before an important audition, Kumiko encourages Reina to be the greatest trumpet player she can be, even if it makes her a villain in the eyes of the rest of the band. She says that she’ll stand by Reina no matter what, and even become a villain with her if that’s what it takes. “Because it’s a confession of love, after all.”

The two girls had been friends for a long time, but acted awkward around each other for most of the series because of an argument they had at the last band contest. Kumiko was scared of facing Reina again, but when the rest of the band began to hate Reina because she was so much better than the other trumpet players, Kumiko knew she had to step in and clumsily declare her love for her former friend when it was most needed. Reina, ever the picture of stoicism, accepts this mess of a confession with a simple nod and goes on to win the audition. The power of love prevails!

When a yandere and a tsundere fall in love, their relationship is bound to be anything but normal. Usagi is quite possessive of his younger lover Misaki and wants him to admit that he loves getting so much attention, but Misaki is too hard-headed to give in. When they’re alone in a ferris wheel carriage together, Usagi confesses his love in a dirty way that’s designed to get on the younger man’s nerves, goading him on until Misaki finally gives in and accepts the feelings he holds inside of himself.

It’s cute, but undeniably awkward. At least Misaki understands that the jealousy he’s been feeling is actually a sign of his love for Usagi! In the end, we’re glad that Usagi and Misaki got to “know more about each other” after such a wacky confession.

Nozaki is a quiet and serious high school student who also happens to be a famous shoujo mangaka on the side! His classmate Sakura has always loved him from afar, but he doesn’t see her as much more than a friend/manga assistant. Monthly Girls’ Nozaki-kun is a slice-of-life anime, so we weren’t exactly expecting a grand shoujo-style outpouring of emotion when protagonist Sakura finally confessed to her crush... but we couldn’t possibly have predicted how he responded.

After an entire series’ worth of tension and Nozaki getting closer and closer to understanding Sakura’s feelings for him, they’re together in the most romantic place a high school anime can provide – watching the fireworks at the local summer festival. She works up the courage and expresses her love! He says he feels the same... he loves fireworks, too. Argh, what a blue balls ending! Sakura seems to take it well, but we’re picking up some seriously bummed “this is fine” vibes from her.

Yui appears to be a sweet girl at first, but she’s actually quite the diva and goes bonkers if she doesn’t get exactly what she wants. The main character, Junichi, finds this out the hard way when she confesses her love to him and he politely rejects her because he’s already in love with someone else. Yui flies into a rage and screams about how he should be just like a trained dog and do whatever she tells him to do because that’s how men are supposed to treat her, dammit!!

Luckily, Junichi survives the onslaught and has a successful relationship with Yukana, the girl he actually likes. Yui comes around in the end and helps both of them admit their true feelings for each other, but she’s still a brat on the outside. We hope, if only for the sake of her future suitors, that she mellows out one day.

Sensational teen star Ryouma could have any woman he wants, but he’s fixated on a shy girl with sparkling eyes who appeared in a wedding commercial with him ten years ago. When it comes time to film a sequel, he insists that the same girl come back to reprise her role so he can meet her just one more time. The shoot is fraught with problems, since she gets flustered when he kisses her for the wedding scene, but in the end it all works out. He finds her backstage and confesses his love for her after all these years! Only then does he find out that she’s actually a boy.

Izumi, the “girl of his dreams”, is the son of a famous acting family and had to fill in for a sick actress ten years ago by crossdressing as a girl. He came back to film the second commercial upon request, but felt terrible deceiving Ryouma. Unfortunately, Ryouma reacts very poorly to this revelation (meaning that he’s incredibly grossed out and mortified), but love prevails in the end. Izumi and Ryouma eventually grow to care about each other for who they really are and they form an adorable yaoi romance together. It just started off with a large bump in the road.

Risa is a tall girl who hides behind sarcasm and toughness to mask her insecurity, and Atsushi is a short guy with a punkish attitude to match. These two started out as frenemies, but after snarking back and forth for so long, they realized that they actually liked each other. However, it’s still hard for them to express their feelings even after they get together.

When they’re on a date at a sporting event, they have a heartfelt conversation in which Atsushi assures Risa that he really does love her. It’s dorky and messy, but genuine. That would be awkward by itself, but what really shoots up the embarrassment meter is that the entire thing was caught on the big screen and everyone in the stadium saw the confession! The announcer even congratulates them! This is one confession that we’re glad never happened to us.

Really, did you think it could have been anyone else? At the very end of Fullmetal Alchemist: Brotherhood, Edward finally confesses his love to his closest friend, Winry. She’s been with him for his whole life, supporting him and his brother both physically and emotionally with her automail mechanic skills and down-to-earth demeanor. Of course, since Ed is a dork who doesn’t know the first thing about romance, he sputters out a confession that sounds like an alchemy recipe: “Equivalent exchange! I’ll give half of my life to you if you give half of yours to me!” Cue giant blushes and scrunched up faces from both of them.

Even though it’s the most awkward anime confession of all time, it’s also one of the most heartwarming and well deserved. After all that Edward and Winry have gone through, getting to see them together in the end is all a fan could ever have asked for. They’re perfect for each other, and it’s this adorably awkward moment that shows how much they truly love one another.