Shinji asks the player if they could just throw the match. Upon getting no positive answer, he tries asking the player's Servant:
Shinji: ".. Then get your Servant to answer me, huh?"
Saber: "Ye gods, of all the rare monsters I have encountered, this is by far the most stupefying."
Saber: "A talking rat! All it mouths is gibberish, but still, a rare and impressive creature!"
Saber: "A talking bear would at least be more fetching. This rat revels in slime and filth!"
Shinji: "Whaa...?! How dare you speak about me like that! You're just a servant!"
Rider: "Hahaha, they have a point, Master."
Shinji: "H-Hey! Whose side are you on?!"
"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.
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.
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/lady! 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."
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.
Hilarious in Hindsight: Cú Chulainn dies commenting that he's glad he saved the girl, but he has to figure out how to not die next time. In Fate/Grand Order he's well known as a "cockroach" because he just won't die.
The discussion of the maiden voyage into the Sakura Labyrinth.
Gilgamesh wonders if Lancer is really a Lancer, musing that maybe she's some extra, rare class. A little later, Lancer calls him "gorgeous class", and he's startled and pleased that HE is the extra, rare class, and takes to calling himself the gorgeous class for the rest of the scene.
Gilgamesh: Now, Hakuno, run! Bwahaha, now isn't the time for you to be dazzled by me!
Hakuno: (While replying Im doing nothing of the sort as definitively as I can, I run to Elizabeth. Im sorry, Elizabeth Im really sorry. Im so sorry I brought this Servant here with me!)
How the whole thing happened in the first place is explained in the material book and it's just as glorious.
AUO Cast-Off [Other]
This is the thing of supreme beauty that Gilgamesh exposes in the fifth chapter.
While writing the script I got excited about the prospect of including a cast-off (nude) scene in the game. One of the staff suggested, For this scene lets have Gil in his swimsuit, and then keep the camera directed up high so we only show bare skin in order to trick the players.
But then another staffer piped up, Huh? You need a nude shot of Gil right? We already have one done you know. It made me feel like I was late to the party.
After that we discovered that some staff had randomly made some extra costumes for the female protagonist outside of work hours including a swimsuit version, gym uniform and even tights. Of course we happily put them all into the game. I want to give a big thanks to Kunimitsu-san from the 3D modeling team. Thanks to you, from the second week onwards in game the protagonist is undoubtedly qualified as a pervert.
Caster's 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.
For those who can't read what's happening, Caster essentially saves you from being deleted by reverting to her nine tailed goddess form to break the laws of space, time, casualty and whatnot to get to you, and essentially beats Moon Cell into submission. However, not wanting to stay in her (understandably) monstrous and evil form, she cuts off eight of her tails and seals them in the Imaginary Number Space. They broke out of there, essentially hijack Moon Cell into 8 Kingdoms, and threaten to turn the entire world into an RPG Maker game if you and Caster don't come to their world. It's extremely hilarious as Hakuno refers to Caster as "The root of this evil" and immediately suspects Caster of being responsible, while Caster is acting innocent and cute to try and deflect suspicion.
Archer: "*Sigh*... Suddenly, I don't feel like doing it."
The first thing Hakuno does after returning from meeting Tamamo's elder form, the sun goddess Amaterasu, is to tease Tamamo with the line "I saw an amazing Caster!"
A scene with Lancer after the battle with the Shinji Tank, which explodes soon after. When Lancer is about to be caught in the explosion, the protagonist saves her. This results in Lancer becoming disoriented and revealing her deredere side, complete with flowery background. Everyone who was watching (Rin, Rani, Sakura, and whatever Servant you selected, even Gilgamesh) is 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."
When you enter the same level as the Shinji Tank, Shinji greets you in what is supposed to be an 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 has to eat her three-course meal. Her breakfast course is enough to put him/her into 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 describes as "fiercer than Vimana's propellant". It's 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 was 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!"
During Rani's chapter, BB introduces Robin, nicknaming him Green Tea and calling him a useless servant, who snarks back at her for it. She proceeds to hit him with a modified water gun that hits forOne hundred million damage, before nonchalantly resurrecting him back.
After Green Archer/Robin 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?
Once you get 30000Sm, Hakuno thinks that it's not enough and 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.
Hakuno: ...Im going to do it. Ill save up as much as I can, and then well see if this Servant has the audacity to call me Hassan again!
Getting 500000Sm finally makes Gilgamesh reject the Hassan name and praise Hakuno... for barely making his treasury into a pittance that is even noticeable. Hakuno is flabbergasted that Gilgamesh is claiming this is his money but has to agree with his argument that since they fight together, their resources are shared too.
Gilgamesh: It is just as well. Were we to convert my treasured swords into Sm, your eyes would fly out of the skull. Hakuno: I see... this is a battle I never had a chance to win in the first place...
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 designer. And she accepts.
For the final door, if you insist on not taking the underwear off, the others will pull a But Thou Must! on Hakuno, and Gilgamesh will give you this gem.
Gilgamesh: Just take it off. Or... Were you not wearing any from the start?
Some of the characters' Secret Gardens have funny comments:
In this game, Kotomine becomes a salesman in the item kiosk. One day, he tells Hakuno to rejoice because there is a new item. Said item? Mapo tofu. If you buy it, your Servant appears and freaks out, wondering if it is for you or for them.
Hakuno: Whats this about all of a sudden? Gilgamesh is feigning calmness, but I can see something grave in his eyes. Im pretty sure this item is for the Masters use, but...
Gilgamesh: I see. Thats fine then. ...No, its nothing. I feel something sinister about it. Dont eat too much of it, all right? If by any chance you become accustomed to the flavor and make it a staple of your diet, I will cut off my contract with you, understand?
More of Gilgamesh's humorous side: if you complete the swimsuit sidequest, Gilgamesh reveals that he personally designed an indoor water park which he called "Thrilling Splash Time". It was never actually built, but he did draw up the designs in great detail. He's so enamored with his own vision that he goes into a half-hour description of the place, over Hakuno's blank look over the mental image of the King of Heroes hanging out in a water park.
You can have Andersen make an evaluation of your servants early in the game. It can be described as a roast to their characters and it's glorious. If you have Caster though, the conversation would turn somber. In a good way.
Near the end of obtaining Gilgamesh's second SG, you can ask "Gil, do you actually love people?". His speechless expression is priceless.
During Jinako's punishment, Hakuno calls her fat. Jinako indignantly exclaims that that one stung more than all of the other attacks put together!
During Passionlip's introduction, if choosing the option about her breasts, Gilgamesh's comments turn from disgust to excitement when commenting on her breasts:
Gilgamesh: While voluptuous women are not to my tastes, when taken to that extreme, my collector's heart is stirred. No matter, it is excellent timing to challenge the summit of what is possible!
After saving Passionlip from Nursery Rhyme and Alice, Passionlip shyly asks if Hakuno wants to be crushed on her ...you know, Hakuno doesn't really understand what she means so she insists the former tell her what she means. Rin and Rani angrily want to put Hakuno on trial for sexual harassment and even create a prosecution program while Leo will stand on their defense as he says he understands Hakuno's feelings.
Type-MOON Ace Omake Theater
The opening of "Tell Me, Blossom-sensei!" begins with Saber, dressed as Santa Claus, singing a very off-key and incomplete version of "Jingle Bells."
Not to mention the Irony of Nero Claudius celebrating a Christian holiday.
Several in "Fight me, Blosson-sensei!": Sakura's Butt-Monkey status getting turned Up to Eleven after the Servants learn she kidnapped both the male and female Hakuno in order to usurp the position of main character because she was sick of playing second fiddle to Rin. When challenged, she "summons" (i.e. dresses up as) Rider and unleashes Blood Fort Andromeda, but is quickly defeated by Saber's Aestus Domus Aurea. In her last-ditch attempt, she transforms into Dark Sakura and declares she needs only one strike to defeat all three, but only chooses Attack for all six of her commands while the Servants, after being coached by Archer, all choose Guard and deliver a Curb-Stomp Battle in retaliation.
It's revealed that male Hakuno is the Master of both Saber and Caster, so they try to wake him up to sort things out. He of course does not want to wake up and Caster hints at getting ready to unleash her Polygamist Castration Fist.