Top 10 Awkward First Kisses in Anime [Best Scenes]

Kokoro Connect is a unique supernatural slice of life with a heavy dose of teenage romance. Five high school students share their daily lives together in the Cultural Research Club but have rather shallow relationships with each other. One day, they start randomly switching bodies, leading to drastic changes in their relationships, for better or for worse.

Two of the members, Taichi and Iori always had a slight attraction to each other but neither felt the need to extend this relationship past friendship. After a life-threatening accident, Iori is unconscious but switches bodies with another girl Inaba. Fearing an imminent death, Iori and Taichi confess their love for each other, and they kiss. It’s a touching moment, except that Taichi is actually kissing Inaba. All three concur that the two stole Inaba’s first kiss in this strangely three-way smooch, but even more awkwardness ensues in the kiss’s aftermath.

Daily Lives of High School Boys is, just as it sounds, a slice of life comedy that tells short scenarios in the lives of your everyday high school boys. Of course, their lives are filled with silliness and irony, where even banal situations can bring the laughs.

As normal high school students, they aren’t immune to everyday awkwardness. In one strange case, a huge bee lands on Hidenori’s mouth à la Silence of the Lambs. Instinctively, Hidenori moves towards Yoshitake. Yoshitake gets an ominous vibe and tries to fight him off, but Hidenori grabs Yoshitake firmly by the shoulders and slams his mouth square onto Yoshitake’s mouth, leaving behind bee guts and nightmare fuel. To make matters worse, a classmate passes by, and the two try to defend their actions until a second bee lands on Hidenori’s lips, and again, there’s only one thing Hidenori can do. File this kiss under “Awkward Ways to Kill a Bee.”

In Chivalry of a Failed Knight, students with magic abilities to form swords from their souls attend a special school to become Magic Knights. The students are rated on their magical ability, but Kurogane Ikki has remarkably low magical skills and has been shunned by his family. He instead does mostly physical training and aims to be the best in a high school fighting tournament so that he can graduate and become a knight despite his mediocre magical skill.

After a stunning victory in a mock battle with his new love interest and roommate Stella Vermillion, a number of girls are now vying for his attention (read: harem). No matter how many girls are interested in Ikki, they will have trouble competing with his younger sister Shizuku, who has an undying love for her kind-hearted brother. Shizuku, who is blessed with high magical ability, enrolls in her brother’s high school and is reunited with Ikki after four long years. Taking a page from the Angelina Jolie playbook, she goes in for an open-mouth make out session with her brother in front of the whole school. Ikki is shocked, but still happy to finally see his little sister, while the rest of the students completely freak out, ending with Shizuku and Stella crossing swords. Unfortunately for Shizuku, her sibling love remains one-sided with Stella around.

B Gata H Kei is an anime teen sex comedy, in which our popular protagonist Yamada is desperately looking to lose her virginity and ultimately have sex with 100 different partners. Despite her lofty goal, Yamada is worried her future sex buddies will tease her because of her inexperience, so she targets a fellow virgin Kosuda to be her first conquest.

As expected, B Gata H Kei has the lion’s share of awkward moments, mostly due to Yamada’s lust-driven, one-track mind, so the unlikely couple doesn’t disappoint with their first kiss. On a Christmas Eve date, after Yamada spends half the night searching for a love hotel, a clueless Kosuda follows her while mulling over whether to kiss her or not. He finally makes a move, but while staring into each other’s eyes, they both start to get cold feet. Our girl Yamada refuses to lose and moves in, head-butting Kosuda hard enough to shed tears. She’s certain she failed, but as the pain subsides, she realizes they are kissing deeply. Mixed emotions of joy and embarrassment send Yamada running off into the night, while Kosuda rejoices in the street.

To put it simply, Senjougahara Hitagi is always awkward, but that’s why we love her! After running into a mysterious crab and being inflicted with weightlessness, it’s no wonder she lost most of her sociability skills. Still, a fellow classmate and half-vampire Arargi Koyomi comes to her rescue and introduces her to Oshino Meme, who identifies the solution to her odd problem. From then on, Senjougahara sees Araragi as her personal savior and inevitably falls for him.

In the twelfth episode of Bakemonogatari, while teasing Araragi, Senjougahara manages to ask him out on a date in an especially awkward fashion, “We’re going on a date. No, that’s wrong. That’s not how it’s said. Shall we go on a date? How about going on a date?”

The resulting date is nothing normal, as they are accompanied by Senjougahara’s father as a chauffer. Regardless, Senjougahara continues to tease Araragi until they make it to their destination: an open spot in the forest to observe a starry sky. Again, Senjougahara asks for a first kiss in the same awkward way she asked for the date. The anime is uncharacteristically modest with the kiss scene, but it has a wonderful indie film vibe that melds awkwardness with a comfortably heart-warming feeling. Add in Shaft’s trademark animation to emote Araragi’s nervousness and anticipation for his first date, and this episode is a beautiful building block in the two’s budding relationship.

The latest Gundam series Iron Blood Orphans from scriptwriter Okada Mari (Anohana, Toradora!) explores heavy themes of child labor and human trafficking on a background of interplanetary warfare. Kudelia Aina Berstein is a young girl from Martian aristocracy hoping for independence from the oppressive rule of Gjallarhorn, a military group from Earth. Kudelia seeks to have negotiations with Earth leaders and is to be escorted by a security firm that employs child workers. Before they can leave Mars, Gjallarhorn attacks the civilian group to thwart Kudelia’s plans, and youngsters are set up to be human sacrifices by their boss. The young laborers fight off Gjallarhorn, rise against their employer, take control of the company, and promise to safely deliver Kudelia to Earth.

Kudelia’s privileged upbringing makes her largely ignorant to the struggles of the impoverished Martian civilians. Aware of this fact, she earnestly wishes to learn more about common folk and tries to become closer to a teenaged Mikazuki Augus, a talented Gundam pilot who has been working hard jobs since he was a child. Both have had little time for romance in their short but starkly different lives.

After a devastating battle with many casualties, Kudelia sees Mikazuki’s hand shaking and tries to console him with an awkward embrace, imitating what she saw her maid doing for younger children. Mikazuki responds with confusion, so Kudelia pulls away to explain herself. One awkward turn deserves another, so Mikazuki smiles and kisses Kudelia, imitating his company’s mentor. Mikazuki keeps his cool, but Kudelia reels off in adorably confused embarrassment. This awkward and charming kiss scene is just one small part of the surprising character development and emotional tugging you’ll find in Iron Blood Orphans.

Introduced with a poignant soliloquy on fate, the first episode of Penguindrum is the definition of a rollercoaster ride of emotions. Kanba and Shoma are twin brothers and have an ill-fated younger sister Himari who is terminally ill and expected to die soon. Kanba begs the doctor to save his sister, declaring he will do anything for her to live, but the doctor can offer no solution to her illness. During a trip to the aquarium, Himari suddenly collapses and dies, but she is mysteriously brought back to life by a crested penguin hat that Shoma bought for Himari as a souvenir. The brothers are overjoyed and promptly bring Himari home.

Himari’s life is extended, but the penguin hat possesses Himari and transports her and the twins to an alternate world. There, she transforms into a condescending princess in a penguin dress and demands the twins cooperate as repayment for extending Himari’s life. After expelling Shoma from the alternate world, the princess reaches into Kanba’s chest to initiate a survival strategy. At the end of the episode, while Shoma is sleeping, Kanba sits next to Himari’s bed, contemplating fate and what it means to be human, and he moves in for an affectionate kiss. Did you feel awkward? Everyone felt awkward after the episode’s surprise ending. After all that buildup, this scene was meant to make you feel uneasy, question everything you just saw, and hopefully watch the rest of the season for the answers to those questions in this psychological drama from Ikuhara Kunihiko (Revolutionary Girl Utena).

In Ore Monogatari!!, Gouda Takeo is not your average high school student. He’s a big, tall, scary-looking guy with the build of a defensive lineman, but he’s the perfect guy for Yamato Rinko, a cute and kind-hearted high school girl who enjoys baking. The two meet after Takeo saves Rinko from a molester on the subway. From then on, we see their sweet and endearing relationship grow in this shoujo, comedy anime.

Along the way, Takeo manages to successfully hold hands with Rinko, but he is disappointed in himself for being so awkward about it. Thinking ahead, he’s certain he needs to practice kissing to avoid future failures. But how can he practice kissing? A pillow? No, it doesn’t have that human feel. Another girl? No way! As a last resort he appeals to his best bud Sunakawa Makoto, who wants nothing to do with kissing practice. Armed with saran wrap, Takeo won’t back down in his mission to make Rinko happy. Poor Suna, we’re sorry, but we can’t help but laugh at your dire circumstances

Honey and Clover is a popular josei romance anime that’ll make you laugh, cry, and cheer. The story follows a dynamic group of university art students, accented by an eccentric sculptor Morita Shinobu who, although talented, hasn’t been able to graduate for eight years. The group is introduced to an adorable 18-year-old prodigy Hagu, who is brought to the university by her cousin, an art professor, so that Hagu can learn more about the world.

Morita becomes infatuated with Hagu and her art, and the two become inspirational to each other’s artwork. Morita tends to be overbearing with his affection due to an overwhelming fondness for cute things, and Hagu is generally timid and socially awkward due to her sheltered upbringing. One day, Morita finds Hagu alone in a field of cherry blossom trees and wraps his scarf around her. While admiring how cute she looks, he unconsciously kisses her. By the time Morita realizes what he had done, he is overcome with embarrassment, screams for dear life, completely wraps the scarf to cover Hagu’s face, and runs off. Hagu is left behind bewildered in this very awkward and very funny moment.

In the ecchi comedy Prison School, the first five males accepted to a previously all-girl high school are caught peeping and sent to the school’s prison for an extreme form of in-school suspension. The boys are submitted to all forms of ridicule and shame while they serve their sentences under the observation of the Underground Student Council.

As the Underground Student Council ultimately wants to get rid of the boys and return to an all-girl environment, they set up a plot to finally have the boys expelled, but our guys aren’t going down without a fight! Kiyoshi steps up to distract their prison guard Hana to get the proof they need to gain their freedom, but due to a series of embarrassing events, Hana has other plans for Kiyoshi.

This leads to that, and Kiyoshi and Hana are facing off bottomless and panties-less in a battle of wills. Eventually both Hana and Kiyoshi break down to the strangeness of their circumstances, but Hana has the upper hand, gives Kiyoshi a sound beating, and then steals his first kiss. Hana declares victory, revealing that she knows about Kiyoshi’s love for another girl but stole his first kiss anyway out of spite. Yes, it’s as strange as it sounds, so you’ll just have to watch it for yourself.