- Dead End Tohka arc:
Shido: AAAAALL RIGHT!!! [pants and wheezes] I rock...
- From the light novel, Hiroto Tonomachi introduces Origami as the third most-wanted girlfriend on the list of the thirteen most-wanted girlfriends. When Shido asks why it's a top thirteen list, Tonomachi says the organiser got thirteenth place, before saying the most-wanted boyfriends goes to 358 places, shocking Shido, who immediately realises the organiser of that list got 358th. When he asks what Tonomachi got, he admits he's the one who got 358th. And then he says that he and Shido were voted best couple.
- Shido and Tohka casually talk while the AST Wizards are shooting down relentlessly on the latter's barrier. And neither of them seem to be worrying a bit during their (unheard) conversation.
- Episode 2 starts with Shido finishing one route of the dating sim Kotori and Reine gave him for his training with dating Spirits. Once the game's credits roll, he screams enthusiastically while slightly stumbling in his movements, implying he did an all-nighter for said route.
Shido: uh... Tobiichi... You look good in those clothes.Tobiichi: It's our uniform.Shido: Tobiichi, I've know you for a long time.Tobiichi: Same here.Shido: Really? So, I'm happy to be in the same class as you and I can't take my eyes off you.Tobiichi: Same here.Shido: And that's not all, I sniff your uniform after school.Tobiichi: Same here.Shido: Really? What a coincidence.Tobiichi: Yes.Shido: Then, would you like to go out with me?Tobiichi: I wouldn't mind. I wouldn't mind going out with you.Shido: Do you mean you like to accompany me somewhere?Tobiichi: That's what you meant? I thought you wanted to date me. Am I wrong?Shido: N-no, you aren't, but...Tobiichi: Okay.
- Shiro “confessing his feelings” for Tobiichii in the second episode of first season:
Shido: Fantastic, I'm relying on perverts.
- Shido attempting to flirt with Tamae "Tama-chan" Okamine-sensei for his training. Her reaction and response is gold. So is Origami's reaction.
- Kotori introduces the rest of the Fraxinus' operating crew, complete with Boss Subtitles Played for Laughs.
Kotori (seconds later): [puts on a cutesy voice] Have faith in your little sister. Now get in there and flirt!
- Shido's punishments whenever he screws up any of the dating aspect. Ranging from revealing his childhood secrets to broadcasting said secrets live on radio. And that's just the start.
- When approaching Tohka, she demands to hear Shido's name. He then shouts that if she's to ask for his name, then she has to give him her name first. There is then an instantaneous cut to Shido getting attacked by Tohka, saying "I knew it!"
- Puppet Yoshino arc:
- When Yoshinon insults Tohka, she rips the puppet off Yoshino's hand and strangles it, thinking it is actually alive.
- Killer Kurumi arc:
Kotori: Shut up! What about blood ties! A real younger sister can't even marry him!
- When Kotori and Mana argue about which of them (foster or real) is the better younger sister to Shido, Kotori drops this gem:
Shido / Mana: Eh......?
- Tohka's appetite. She is even able to eat frying pans.
- Sister Itsuka arc: When Origami asks if Tohka's okay, Shido initially took it as proof that the former is now okay with the latter, but after saying she's fine, Origami was disappointed.
- Lily Miku arc:
Hiroto: That’s cheating, Itsuka you bastard!?
- When Hiroto Tonomachi expresses shock that Shido doesn't know who Miku Izayoi is, he claims that within their generation "there's no one other than stupid Itsuka-kun that doesn’t know about the super national idol Miku-tan", and that if he were to be proven wrong, he'd kneel down on the ground and eat spaghetti with his ass. Without skipping a beat, Shido promptly asks Tohka.
- Ladies and Gentlemen, I present to you, Shiori! In order for Shido to approach Miku, who Does Not Like Men, he has to cross-dress as a girl. He even needs to practice of acting as a girl before approaching Miku. It works well enough that Miku and the schoolmates doesn't suspect the cross-dressing in the slightest. This doesn't stop Tohka, Origami, Yoshino and Kurumi from seeing through his cross-dressing at first sight.
Yoshinon: Yahahaha, is that perhaps Shido-kun? It really suits you. Why don't you just wear the top and take the bottom. There's demand for that you know?
- The best part is what Origami does the moment she sees 'Shiori'. She start taking pictures of her in different angle, which causes Shiori screams like a real girl.
- Another moment is when Reine brings Yoshino to the Maid cafe that Shiori's working and seemingly recognize 'her' immediately based on Yoshinon's words. Shiori could only cower 'herself' in shame knowing that Yoshino have seen something she shouldn't be seeing:
- The three girls handing Tohka a tambourine. With epic background music.
- Even during the Darkest Hour, there was one. It turns out that despite most of the Fraxinus crew falling under Miku's Mind Control, Kyouhei remained sane and went along with it because he's in his happy place.
- Truth Miku arc:
- Miku, who is controlling Yoshino as well as the Yamai sisters, orders them to eliminate the enemy Wizards. Problem is, they also count Mana, who's there backing Shido up as an enemy Wizard. What does Mana do? Bumps into Ryouko's squad and essentially says "Tag, you're it!"
- While poking around Miku's things, Kurumi finds a bra that's the size of her head and goes, You Have Got to Be Kidding Me!
- The epilogue of season 2 has Miku singing one of her previous songs when she was still Tsukino Yoimachi. After a long Heartwarming Moment, she proceeds to thank Shido by calling him "Darling". Cue her audience's utter confusion as well as this exchange:
Yuzuru: Repeat. Darling?
Yoshinon: Don't tell me...
Tohka: Speaking of which, Miku called you that earlier too, didn't she? Shido, what does darling mean?
Shido: Well, that's...
Yuzuru: Confirmation. Shido.
Shido: Uhhh... [confused while looking Miku waving at him]
Kotori: *laughs* You're so popular, Shido.
Shido: [bowed sluggish]
- Search Natsumi arc: Tohka and Yamai sisters halted Miku's attempt to give Shidou a goodbye kiss, only to end up getting chased off by Miku's attempt to do a proxy kiss with Tohka.
- Change Natsumi arc:
- After saving Natsumi from Ellen and taken her into an underground facility owned by Ratatoskr, Shido and his friends decide to open up Natsumi's heart despite Natsumi revealing her being a true form.
- After getting a massage treatment by Miku, a haircut by the Yamai Twins, and dressing her up by everyone, Natsumi is going to be given makeup treatment by the 'last assassin' who actually turns out to be Shiori note . Natsumi did not take it well even calling Shido a pervert when 'Shiori' reveal herself. Miku and Kotori seems to be giggling about it knowing that Shido gets hurt by Natsumi after Shiori's reveal outside the room.
- The entire bad negative thinking of Natsumi when meeting with some people and getting a lot of misunderstanding when she picks up their sentences:
- Tonomachi Hiroto:
"I got dizzy!" -> To get dizzy... Meaning: "Close to collapsing from dizziness." -> "I am about to collapse from dizziness by looking at you!" -> "I feel sick just by looking at you, ugly!"Natsumi: I knewwwwwwwww ittttttt!!
- Kyohei Kannazuki:
"Natsumi has a nice body!" -> "Natsumi’s body is good" -> "Your looks are regretful but, there are no problems with the functions." -> "Seems like your organs would sell pretty well."Natsumi: Mur-murderer!?
- And during lunch time:
"Would you like potatoes with that?" -> Potato in this case = Fried potatoes. -> Getting fat is very easy with the combination of carbohydrates and oil. -> "That seedy-looking body might become a tad better if you add more flab, won’t it?"Natsumi: God. Damn. Ittttttttttt!
- Tonomachi Hiroto:
- Angel Tobiichi arc: Natsumi in her grown up form teases Kotori after the later tells Natsumi that she should try to do something about her using her transformational powers as crutch to combat her complex. Having stepped on that landmine, Kotori angrily points out that Natsumi's real form is even scrawnier than she is, only to try and backpedal once Natsumi turns on the waterworks.
Kotori: Ugh...Fine, I'm scrawnier than you, okay?!Natsumi: Ahhahahahahahaha-! Scrawny, Scrawny! Kotori's scrawny! (runs away)Kotori: Wha-...I...You tricked me you little-!
- Turns out that Kotori's right. Natsumi's real height is actually 1cm shorter than Kotori's.
- Devil Tobiichi arc:
- past!Kurumi wearing an eyepatch and present!Kurumi seeing it as an Old Shame with Shido not getting any clear answers.
- In the Epilogue, Origami helps Shido wipe his tears... with her own skirt! Then it turns out she's wearing a dark blue school swimsuit and brought along a dog ear headband, dog tail and also the leather collar. The same items that she wore during Shido's first failed break up date. Guess there are some things that never changed.
- Disaster Itsuka arc:
Tobiichi: I don’t mind being last. Also, I want to know if the medical room has a lock. It’s even better if the room is sound-proofed.The moment Origami said that, everyone twitched their eyebrows.
- A Not Himself Shido flirts with anything he sees, including Ellen! Hilarity Ensues
- Westcott's surprised reaction towards Ellen's enthusiasm thanks to the above events.
- Drunk Origami is this in spades
- Even earlier, Origami asked whether the medical room Shidou was in is lockable and sound-proofed. This instantly causes all the girls to change their mind about taking turns entering the room.
- A Not Himself Shido flirts with anything he sees, including Ellen! Hilarity Ensues
- Creation Nia arc: Nia, just Nia's antics for most of the volume.
- Planet Mukuro arc: How Nia just slides by the Wham Line she dropped at the end of the previous volume over mentioning how all the Spirit were formerly human.
- Family Mukuro arc:
- Back in last volume, Mukuro acted completely indifferent towards Shidou's self-introductory to establish a master-slave relationship* . This becomes a Brick Joke after her emotions were unlocked when Mukuro pops into view from a portal and accepts said offer to become his "flesh slave" and asks him to enlighten her to its meaning. Needless to say, everyone dropped their jaws to her response.
- At the start of Shidou's date with Mukuro, they decided to give Mukuro a makeover at Shido's house due to her incredibly conspicuous Astral Dress and her incredibly long hair. Shidou borrowed Kotori's clothes which Mukuro tried to wear herself... except that it doesn't fit her chest. Kotori's reaction to that is "a sound of silence, as if attempting to restrain a certain unspeakable emotion with all her might".
- Remember how dangerous Tohka was in Volume 7? Ever wonder why she has her hands in the shaping of a heart in volume 15? Origami ended up tricking her into going on a date with Shido, saying that it was the only way to rectify the disgrace she suffered from last time. They ended up going to a Maid Cafe, where a waitress teaches her a charm for making food taste better by holding her hands in the shape of a heart and yelling "Moe Moe Kyun". Tohka falls for it and ends up believing that it is a one hit kill technique.
- Other Media:
"A pervert. That is someone who likes it when the bud of rose blossoms, or when a butterfly moves its wings at night. I can't stop za loneliness! Who knew I was like this?"
- From the video game adaptation, people had a little chuckle when they saw the "Data Install" sign.
- Episode 13 of the first season is a goldmine of hilarious moments, which is actually based from Date A Live Encore Light Novel, a spin-off of the Date A Live novel. To wit:
- The narrator is known for zany lines in the opening animation, but this one takes the cake:
- The entire Epic Fail breakup date between Shido and Origami:
- In Shido's first breakup attempt, Shido note ask Origami to change into a School Swimsuit with dog ears and tail, and asking her to walk on all fours. Which she does.
- Right after that, she rips off Shido's belt, puts it around her neck like a leash and starts acting like a dog. Shido just breaks down and desperately tries to apologize. She doesn't care a bit.
Origami: Woof! *pant pant* Woof!
- Later in the restaurant, Shido attempting to get a reaction out of Origami by successively pretending he's a paedophile / momcon / siscon / playboy. Turns out it's to disgust her so she rejects her love for him. With little effect.
- The final kicker is when Origami was going to the bathroom, Shido ask Origami to do it her. Once again...she does. Shido tries to stop her but he accidentally takes down Origami's skirt. And Origami just stands there showing her black panties like it was noting, much to everyone's shock.
Origami: You want it on you? Or do you want to ***?Shido: PARDON?!Kotori: (Divekicks him) You're one to talk!
- To make up for accidentally telling Tohka he hates her and running into a bout with Origami, Shido takes her to the arcades. Where she promptly breaks some machines.
- After her date with Shido, Tohka comes to school unexpectedly happy. When asked why, she blurts out stuff that could be mistaken for sex while having an ecstatic face. Cue her schoolmates' bewilderment.
- The above leads to the class turning to Shido, who tries to claim his innocence... at least until a naked picture of Tohka slips out from his pocket. When he takes it back from Ai, he realizes what it is, and a oh YEAH sound effect can be heard.
- The entire Date A Quest short story. With Shido being the "princess", Kotori Breaking the Fourth Wall, and Origami taking Shido's pictures with Shido snarking at the entire thing.