- More or less any moment involving the Literature Girl.
- Episode Five's internal-Big "NO!" moment, when poor Hidenori realises she's standing right behind him again. The screaming is perfect.
- Episode Seven is one long Humiliation Conga for the poor girl. In order of events: (1) the wind blows away the manuscript of her novel, (2) when she starts chasing after it she trips and falls and bruise her hand, (3) she struggles to open an box of bandaids for her bruise before finally giving up, (4) when trying to drink a bottle of water to regain her composure she suddenly starts choking on it, (5) she suffers a choking fit and ends up blowing a large amount of snot out of her nose, (6) she ends up tripping and crashing into Hidenori, and finally (7) she starts bawling her eyes out after the string of humiliation. The entire time, Hidenori can barely contain his laughter. When he tries to reassure her with encouraging words, he ends up accidentally headbutting her and knocking her out.
- Episode Ten's hilarious Chase Scene involving the two of them. And the reason she wanted to chase him down so badly? To yell at Hidenori that the guy she was with when he saw her wasn't her boyfriend.
- Any segment where Hidenori Internal Monologues, really. They show off Tomokazu Sugita's skills to the fullest.
Hidenori: "This mole hair... is proof of her loneliness."
- The mole-hair girl monologue from episode three.
- The RPG-roleplay segment at the beginning of episode 2.Hidenori/Jack: Cha-ra-ra-raaa, cha-ra-ra-raaa, cha-ra-ra-ra, cha-ra-ra-ra, chan-cha-ra-ra-ra-ra, chan-cha-ra-ra-ra-ra-ra-ra-ra-ra-ra-RA-RA-RA-RA-RA-RA-RA CHAAAAAN-chaaaaan![Beat]Hidenori/Jack: Jack has joined your party.Tadakuni: Too long! What music was that!?Yoshitake: You know, it's that music that plays in RPGs when someone joins your party—Tadakuni: Don't explain!!
- Jack even gets a Call-Back in Episode 7 when he randomly joins the party without any context.
- In "High School Boy and Drop Kicks", Hidenori meets a girl who dropkicks him because she thought he was her friend Kiyohiko. When he actually comes by, Hidenori tells him to take action and take payback for all of the times she's kicked him, and then accidentally throws them both into the river. Kiyohiko's response to any of this? He cries and tells his friend that no one has ever said that before, and instantly befriends Hidenori. The girl is left wondering if this entire scenario was "Boy Meets Boy".
- The last main skit of the anime, "High School Boys and...", while being nothing short of a Heartwarming Moment for tying up most loose ends after the main crew graduate, ends with Tadakuni waking up after seeing Nago become the "Convex Mirror Girl" again, revealing that the entire segment was a dream.
- The Once an Episode credits gag for the anime, where a picture of Yoshitake holding a tie increases in number starting from episode 2 (and the numbers somehow correspond to the number of the episode). There are episodes that particularly stand out:
- The ninth episode features a parody of Andy Warhol's art pieces, having nine Yoshitakes multicolored and positioned.
- The show goes on to make a 10 by 10 square of multicolored Yoshitakes for the tenth one.
- On the eleventh, they only take one Yoshitake, but they blow it up to fit half of the screen.
- On the twelfth and final episode, they instead position a number of default colored Yoshitake pictures to make the word "END".
- Who could ever forget this one where Hidenori and Yoshitake dressed Tadakuni with his sister's clothes in 'Highschool Boys and Skirts' when she went to the room and saw the ordeal. Cue Freak out from the boys.
- In "High School Boys and Mochi Soup", where the three protagonists all happen to be choking on mochi despite the content warnings.
- Cue Tadakuni getting punched in the stomach by his sister.
- Their wacky dubbing at "High School Boys and Dubbing"
- In "High School Boys and Careers", where the students give a career questionnaire and their answers are completely outrageous. Honorable mentions goes to "Teacher's Wife" and "I don't want to become a lawyer." The teacher's reactions to this are extremely priceless.
- "High School Boys and Indoor Adventures" has a parody of a typical TV show's "Last time on..." segment, set with short introduction clips of all the characters. But since Yoshitake plays two characters, and Hidenori plays four of them...
Funny / Daily Lives of High School Boys