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- Episode 1:
Yukino: I see danger to my person in those vulgar eyes looking at me full of ulterior motives.
- Yukino's rebuttal to Shizuka's proposition and Hachiman's inner response.
Hachiman: I'm not looking at you, and especially not that ever-so-modest chest of yours. [looks at her chest] I'm truly being honest here.
- Hachiman decides to drive away Yukino by intimidating her. While his reason is more or less sensible, his method consisted of staring at her and growling. For added comic effect, Hachiman cowered after just one Death Glare from Yukino.
- Yukino delivers a speech for Yui about skills, talents and hardwork. Yui's response "you're so cool!" caught Yukino off guard so much it left her slack-jawed.
- Episode 2, Yukino provides constructive (albeit rather harsh) criticism of Zaimokuza's light novel. The latter is completely crushed and tries to seek some consolation from Hachiman.Zaimokuza: Hachiman, you can understand me, right?
(Hachiman gently smiles)
Hachiman: So what was that a ripoff of, anyway?
(Zaimokuza grabs his chest in pain and starts rolling around)
Yukino: You're ruthless.
- What's so funny about it is that while Yukino spent some time tearing Zaimokuza's work apart, it only takes one sentence for Hachiman to break the guy.
- Hachiman admits that he keeps a list of people he wants to kill and Yukino's name is on two of the pages.
- Episode 3:
- In the opening, Hachiman is off playing tennis by himself when an errant ball is flying towards him. He braces himself for the hit, but it actually lands a little ways off. He sends the ball back, and resumes his own playing... only to have a ball he served hit one on the ground and launch it, and that ball smacks him in the face.
- At the end, Yui and Yukino are walking off together while Hachiman is with Saika, and Hachiman curses the rom-com gods for the situation. He returns to the clubroom to find Yui and Yukino in the middle of changing clothes, and gets a racket to the face. He praises the rom-com gods for that situation.
- Episode 4, Yukino's summations of the chain mail suspects, which even Hachimon finds harsh.Hayato: Tobe looks like a bad guy, but he's the most easygoing, and the mood maker. He's always the most proactive in events like these. He's a good guy.
Yukino: So he's a class clown who isn't good at anything but making a scene. [Beat] What's wrong? Continue.
Hayato: Uh, Yamato is really level-headed and a good listener. He does things at his own pace and puts people at ease. He's a good guy.
Yukino: So he's dense and indecisive.
Hayato: [visibly anxious] Ooka is great with people. He's good-natured and always helping someone out. He's a good guy—
Yukino: So he reads people's moods like a weathervane. Any one of these people could be the culprit.
- Episode 5: Nyaa. Nyaaa... Nyaaaaaa!
- Episode 6:
- Komachi the good wingman.
- Hachiman's reaction to Haruno's teasing:Hachiman: Too close! Too close! Too close— hmm, smells nice.
- Yukino timidly asks Hachiman to stay with her while she chooses Yui's present but he reiterates that he looks suspicious due to being a lone male in women's shops. To solve the problem, Yukino gives him permission to be her boyfriend for the day in order to look like a couple and avoid suspicious. Since we're talking about Yukino, Hachiman's reaction is very appropriate.Hachiman: Talk about condescending.
- Yukino comparing Hachiman to an air conditioner, delivered in her usual matter-of-fact way:Yukino: If all you can do with an atmosphere is to breathe it, any air conditioner out there is way ahead of you.
- Episode 7:
- Shizuka spams Hachiman with emails, thoroughly scaring him in the process.Hachiman: I feel I'm beginning to understand why Hiratsuka-sensei isn't married yet. Just how much does she like me?
- Komachi's short gambit to lure Hachiman to a club trip, and his subsequent reaction to that.
- Yukino almost responds to that silly greeting before catching herself at the last moment.
- A bit of introspection on Sensei's past.
- She then deliberately splits of the elementary school boys and girls, Hachimon lampshading the pettiness.
- Hachiman's associations on laurier leaf.
- Shizuka spams Hachiman with emails, thoroughly scaring him in the process.
- Episode 8
- Yukino's A-Cup Angst being thoroughly commented upon by Komachi AND Hachiman. What really sells the moment is how Yukino genuinely had no idea what they were talking about in the beginning and when she finally does she immediately covers her chest with her hands and launches into a long rambling dissertation on how her breast size absolutely does not bother her in the least and how, since they're on the subject, you should judge a woman's physical attractiveness based on the balance of their bodies on a whole and not on a single attribute, all interspersed with shots of Yui's, Yumiko's and Shizuka's (all considerably larger) busts.
- Hayama asking what's The Plan to help Rumi. All while wearing an incredibly ridiculous outfit.
- Episode 9:
Komachi: It's your head that's broken, Bro.
- In the opening, Hachiman is lying on the sofa, anguishing over the short amount of time before school starts again. He rocks back and forth until he rolls too far and falls off the sofa... at which point the scene suddenly cuts to the intro sequence.
- Hachiman uses a phone app on Yui's dog to decode its bark. He constantly gets "Let's go play!" and starts wondering if his app is broken. Then he tries barking himself and gets "I don't want to work, master!"
- Elaborated further in Volume 5: Hachiman then downloads a similar app to decode Kamakura's meowing and gets "Itchy. Tasty"
- Episode 11:
- The yaoi rendition of The Little Prince. Which gets rave reviews from what appears to be an all-female audience...Hachiman: Even the original lines sound like BL now...
- Hachiman and Yukino bickering over the walkie talkie about Sagami failing her opening speech.Yukino: Hikigaya, give her signal to go on.
Hachiman: [irritated] I've been for some time already. She doesn't notice me.
Yukino: Oh? I guess I picked the wrong person for the job, then.
Hachiman: Are you ridiculing my lack of presence?
Yukino: I'm doing nothing of the sort. Anyway, where are you? In the audience?
Hachiman: You are ridiculing me! Besides, you can actually see me!
Committee Member: Umm, Yukinoshita-san, we can hear you.
- The yaoi rendition of The Little Prince. Which gets rave reviews from what appears to be an all-female audience...
- Essentially all of Sport Festival in Episode 13.
- OVA 1
- Hiratsuka-Sensei is forced to ask the Service Club for help on an article for marriages, since she knows nothing about marriage, Hilarity Ensues
- The Bride Point competition run by Komachi ends with a round of Bridal Dresses. When she is about to declare herself the winner, Hiratsuka stares Komachi down until she declares her the winner. Komachi is left a crying mess complaining about how scary Hiratsuka is to Hachiman.
- A minor one in the updated Season 2 opening. We see a shot of Hiratsuka posing with her (illegally parked) car on a bridge. While it's easy to dismiss this as normal anime opening shenanigans, the next cut has her bowing her head to the police.
- Episode 1:
- Ebina making a request to the Service Club regarding Tobe while showing an uncharacteristic shyness as she mentions his name. Due to the previous visit, Yui gets immediately excited for this. Turns out it was another of Ebina's Yaoi ramblings. Yui's reaction is priceless.
- When the trio ask Tobe what is his best attributes he says this:Tobe: I'm friends with Hayato-kun?
Yui: You are already relying on someone else!
- Yukino meets ramen.
- Episode 4:
- This scene with Hachiman bumping into Iroha in the mall.
- Episode 6:
- Iroha's spiel about asking for help, you can only ask for help with little things and mistakes that make you seem cute, big things just make you a pain. Hachimon lampshades how manipulative she is.
- Basically the entirety of the Christmas event meeting, with Kaihin Sogo's heavy use of random buzzwords and Tamanawa's erratic hand movements. With the second season being far more focused on the drama aspect of the series, this episode was almost like a return to season 1's style.
- Episode 9
- The start of the episode where Hikigaya is rolling around flustered and internally embarrassed from his Heartwarming Moment from the previous episode.
- Komachi doing an impression of Hachiman and the latter asking what wrong with her.
- Iroha hands over the bag she's carrying to Hachiman without breaking speech, who wordlessly accepts it as if carrying her stuff is the most natural thing in the world. It's such a coupley gesture that Yukino and Yui can't help but just stare at it with a Jaw Drop for a second too long.
- Hachiman, Yui, Yukino, and Iroha all decide to go to Destiny Land, but they have an extra ticket, so Iroha decides to invite someone else, which she keeps as a secret. When they all meet for the trip we see that she's invited Hayato... and a camera shift reveals that Yumiko, Tobe, and Ebina are also coming along.
- Tobe ruining Yumiko's and Iroha's advances on Hayato after he (Tobe) asks Hayato to sit alongside him in the roller coaster because he's too scared of it.
- Episode 9's next-episode preview. Rumirumi. 'Nuff said.
- Episode 10
- The idea of making homemade cakes for the audience at the Christmas Event can be considered an Epic Fail if you notice that a huge part of the audience are elders. All that sugar can't be good for them.
- Yukino asking Yui to stay away from the cakes she was baking. She even prohibits Yui from touching them, let alone taking a look at them!
- Komachi insulting Hachiman and using his own name as an insult after he nearly ruins her excuse to leave him alone with Yukino at the festival. The latter ends up giggling about it.Yukino' Baka (giggle), bokenasu, Hachiman...
- Hayato accidentally referring to Yukino by her name.Hayato: There, there. It looks like Yukino-chan rushed here as soon as she could... [[beat] What will you have, Yukinoshita-san?
- What sold the above scene was Yukino's face at him during the beat.
- Episode 11
- Yukino stopping Iroha's teasing with a Death Glare and a single sentence.
- Iroha's "seductive recon" example full with an innocent voice and sparkles around her.Yui: How do you seduce someone with that?
Iroha: [clears her throat and looks at Hachiman] Senpai, are you dating anyone right now?
Hachiman: [blushing] ...N-No... not really.
- Episode 12
- Saki vs. Yumiko.
- While we see everyone in Sobu working on their chocolates, from time to time, the scene cuts to Kaihin Sogo who haven't even started because Tamanawa is giving one of his speeches again.
- Kaori making Tamanawa and four girls close to Hachiman become visibly anxious when she asks Hachiman if she ever gave him chocolates in the past and promising to give him that year.
- And then Haruna dropping the bomb on the situation by commenting about how Yukino gave Hayato a chocolate in the past.
- Episode 13
- Episode 1
- Hachiman's thoughts when walking past the diner where Saki and her sister are sitting.Hachiman: When I think of familiar young girls, I think of Keika Kawasaki. And, when I think of someone completely coddling her, I think of... that's right, that Kawa-whoever!
- Again, while sitting at the same table as Keika and Saki:Hachiman: (to Keika) Want a bite?Keika: Yeah! This is why I like you, Hachiman!Hachiman: Yes, yes, I know you do. But boys are going to immediately misunderstand that sort of nonchalant touching, so don't do that to anyone else, okay?Keika: Okay! I'll only do that to you, Hachiman!Hachiman: (thinks) Oh man, if she used her girlish charms as a terrorist, she would already know the powerful words that capture a man's heart! This child is to be feared!
- Hachiman's thoughts when walking past the diner where Saki and her sister are sitting.
- Episode 7
- The 'rap' battle between Hachiman and Tamanawa while discussing the former's prom ideas. What makes it even funnier is not only Orimoto's ad-libbing Yes-Man catchphrase after one finishes their verse, but also Yui's surprised look at Hachiman starting it off, then randomly taking out her phone to record the whole thing.
- The Drama CDs are, in summary, side event flags where the most recurring characters of the series get together due to a random reason. These specials are filled with running gags, ship teases, and pure comedy. Each character spends the entire time Establishing Character Moment.
- The Running Gag with Iroha's constant "rejections" of Hachiman starting in Zoku!.