- 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: AAAAALL RIGHT!!! [pants and wheezes] I rock...
- 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.
Shido: Fantastic, I'm relying on perverts.
Kotori (seconds later): [puts on a cutesy voice] Have faith in your little sister. Now get in there and flirt!
- 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!"
- 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 Kotori and Mana argue about which of them (foster or real) is the better younger sister to Shido, Kotori drops this gem:
Kotori: Shut up! What about blood ties! A real younger sister can't even marry him!
Shido / Mana: Eh......?
- Tohka's appetite. She is even able to eat frying pans.
- 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 doesnít 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.
Hiroto: Thatís cheating, Itsuka you bastard!?
- 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. To wit:
- Shido attempting to get a reaction out of Origami by successively pretending he's a lolicon / momcon / siscon / playboy. Turns out it's to disgust her so she rejects her love for him. With little effect.
- The narrator is known for zany lines in the opening animation, but this one takes the cake:
"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?"
- Shido taking Origami out on a date with lots of people around, asking her 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 his 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!
- 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.
- In volume 7, 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 Shidou up as an enemy Wizard. What does Mana do? Bumps into Ryouko's squad and essentially says "Tag, you're it!"
- In the opening of volume 10, 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?!
Ahhahahahahahaha-! Scrawny, Scrawny! Kotori's scrawny! (runs away)
Kotori: Wha-...I...You tricked me you little-!
- 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.
- 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 three girls handing Tohka a tambourine. With epic background music.
- 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]
- When Yoshinon insults Tohka, she rips the puppet off Yoshino's hand and strangles it, thinking it is actually alive.
- Volume 11: past!Kurumi wearing an eyepatch and present!Kurumi seeing it as an Old Shame with Shido not getting any clear answers.
- Volume 12: 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.