I get chuckles from seeing Shido and Tohka just plain talk while the AST is shooting down relentlessly on the latter's barrier. And neither of them seem to be worrying a bit during their (unheard) conversation.
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'spunishments 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!
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: