- "Rin goes from comatose to bitch in three seconds flat."
- When Archer tells you about his greatest triumph, saving 10,000 people from a nuclear reactor meltdown, the protagonist says that at least he got a good tan out of it. Archer's response?
Archer: "Ha. Ha. Ha. I don't think even Rin Tousaka could say something so cruel."
- Talk to the Student Council NPC in charge of the Library on the 3rd day of the 2nd week. She tells you about using the triangle button to skip dialogue, and starts, in her own words, "whining relentlessly about my boyfriend" so you can practice. The whole rant is comedy gold.
- The kicker is if you sit through the whole thing. After a Beat, she adds that you can review any conversation you've just had by hitting square, but "you shouldn't do that now".
- If your Servant is Saber, the enemy Archer repeatedly insults her at one point, and she fixates on the fact he called her 'princess'. Apparently, she's worried you'll start using that as a pet name.
- Speaking to Saber during the 4th week. She decides to start talking about her favorite play. Two hours later, she's not even done with the prologue. It's terrible, and it's implied she wrote it.
- If you choose to save Rin, talk to Archer during the 4th week. It begins with Archer falling out of his chair after you ask your first question. All but the last question you can ask after that give some pretty hilarious responses.
- During one of your early conversations with Saber, you can ask about her True Name. She actually starts to tell you, then suddenly realizes what she's doing and backpedals hilariously.
Saber: "Erase all thoughts of Lu- from your mind!"
- Late in the game, one of Saber's conversations mentions that she once wrestled a lion while naked. Hilariously, the protagonist isn't bothered by the wrestling or the lion part, but it's the naked part that throws them off.
"Isn't there something obscene tucked away in the middle of that line?!"
- Just like on the 4th week, if you chose to save Rin, you can talk to Archer on the 6th week. The first question you ask him is "Is Rin your ex-girlfriend?" and it gets funnier from there. For starters, the protagonist calls him a "playboy of the highest caliber".
- When asked if you prefer comics or manga, you can select bande dessinee. Response: "...How very hipster of you."
- The lunch scene is awkward comedy straight from a school manga; of the Yuri Genre no less, if your MC is female. Your Servant clinches it, from Archer bluntly informing you that your oblivious reaction was "a dick move" to Caster's later conversation in your room, including one hilariously fourth-wall-breaking option.
Choice Three: ... I think I should save now.
- During a Week One conversation with Archer, one dialogue choice results in the MC despairing of their bitter, cynical, sarcastic new Servant and wishing you could swap him out for a "beautiful, graceful, respectful" one. Archer informs you that they were fresh out of those, but not before cracking up at your expense.
- One of the NPCs in the courtyard has a Command Seal tramp stamp. Also, he's male. Yeah, he's not too happy about it.
- On Rani's path, your conversation with her in the Infirmary is interrupted by Gatou, who doesn't seem to know the MC is a Celibate Hero.
Gatou: I did not wish to believe it, but a clandestine tryst is being held!Gatou: Young man! Follow the path of abstinence and righteousness!
- During Rani's mana transfer, the typically-unshakable Archer is... somewhat shaken. Rani, on the other hand, is indifferent until she realizes you're peeking.
Archer: Wait a second, I thought you were from Egypt, not Babylon! You don't have to touch me there...
- An early conversation with Archer leads to the following narration from the player character:
Archer may be a pain in the ass, but all he's doing is making me think about what being a Master truly means. He's not "topping from the bottom."
- The powers that Arcueid would have had if summoned with her true class instead than as Berserker are: a Blood Drinker that drains the life from her opponent; a Life Eater that consumes her foe's vitality; a Financial Crisis where electronic trading decimates an entire nation's economy.
- Meeting with Rin after completing the prologue involves her mistaking the protagonist for an NPC, and attempting to find out how good the simulation design is by groping the protagonist, then asking why he/she is blushing. Then her servant explains. Rin's reaction is priceless.
- How does Gilgamesh defeat (Devil) Lancer? He strips naked and wins by hormonal overload. Translation here.
Gilgamesh: "A.U.O.! CASTOFF!"
- Don't forget Lancer's reaction.
Gilgamesh: Now, Hakuno, run! Bwahaha, now isn't the time for you to be dazzled by me!Hakuno: (While replying “I’m doing nothing of the sort” as definitively as I can, I run to Elizabeth. I’m sorry, Elizabeth…I’m really sorry. I’m so sorry I brought this Servant here with me!)
- And what happens latter:
- Casters Servant ending. Where she saves you from being deleted by making 8 copies of herself. The horrified/scared reaction of both versions of the Protagonist says it all.
- Her ending 
- In Extra, Caster talks about having a "Polygamist Castration Fist". In CCC, it's one of her specials.
- During the Bonus Boss fight with Archer and Rin, we get this banter before Archer unleashes Unlimited Blade Works:
Rin: "Archer, do that thing! I am the bone of my sword!"Archer: "*Sigh*... Suddenly, I don't feel like doing it."
- A scene with Lancer after the battle with the Shinji Tank, which explodes soon after. When Lancer was about to be caught in the explosion, the protagonist saves her. The result, Lancer becoming disoriented, revealing her deredere side, complete with flowery background. Everyone who was watching (Rin, Rani, Sakura, and whatever Servant you selected even Gilgamesh!) was not amused... except Archer.
Lancer: "Hey, darling. I had a weird dream. You and I, we were fighting, and after some evil, heartless women brainwashed you, I was about to die in the blast of an idiot's malfunctioning weapon. But then you came running, saved me, and told me 'If you were to die, I would not want to keep living either, baby."
Hakuno: (Their cold stares pierce my heart without mercy.) No, no, you’re wrong. This all a misunderstanding, just a misunderstanding…
- And Hakuno's reaction:
- In a scene before that when you enter the same level as the Shinji Tank, Shinji greets you in a suppose to be over the top and epic manner. Gilgamesh just laughs at him.
- To top it off, it's obvious from Gilgamesh's non-Large Ham laugh that he wasn't humored at all. He felt that what happened was so stupid that he forced himself to react.
- To advance through Lancer's level, the protagonist have to eat her three course meal. Her breakfast course is enough to get him/her a literal BSOD. When you arrive at her lunch course, the Mission Control sends you a food eating freeware so the protagonist doesn't have to torture themselves eating things that Gilgamesh describe as "fiercer than Vimana's propellant". It shaped like Shinji. Shinji, of course, protests over it.
- The dinner table is worse; a full course meal. Pushing back the horrible taste with a happy memory of when the student council are talking about what they should have for lunch, the protagonist has a pseudo-dying dream about Julius' curry. Your Servant jerks you away by basically saying, "stay away from that light!"
- After Green Archer gives you a pack of detailed data about BB because she never said he couldn't, Hakuno starts thinking about how good it would be to have Archer as an ally.Then this happens:
Archer: Now then. Since we've covered all there is to talk about, shall we start killing each other now?Hakuno: — wait. What?
- Once you get 30000Sm, Hakuno thinks that it's not enough and [[Fiction500 Gilgamesh]] says that "not enough" hardly covers it. He tells her to get more money but she explains that she can only get money through fighting. Gilgamesh is surprised and asks if that "thin, meager, lowly, miserable treasury" is everything she owns. When she answers yes, Gilgamesh actually starts crying.
Gilgamesh: ……………………………no, tears come to my eyes…What an impoverished woman you are…not just in your physique, but in your purse as well…and your looks… well, those are average at least.
- He apologizes because he doesn't understand the concept of poverty and calls her Hassan because they're both unfortunate (and tells her not to approach him because poverty appears contagious). He then makes an Incredibly Lame Pun about Hassan being the only who's bankrupt (hasan). Needless to say, Hakuno was not amused.
- To advance through Rani's level, the protagonist needs to remove their underwear. It becomes even more hilarious if you're the female protagonist because Leo asks Julius to bring a camera.
- Gilgamesh asks Rani to become his underwear's designer. And she accepts it.
- Some of the characters' Secret Gardens have funny comments:
- Gilgamesh's comment on his three sizes: B94/W73/H93 “A golden king should have a golden body. It may be too glorious for your eyes, but if you wish to see a Cast Off, prepare to be amazed.”
- Rani's comment on her underwear: Are you seriously asking that? “I will say it however many times necessary. Underwear – is – forbidden.”