Among all the serious problems of finding himself as a penniless minor in an unknown country in an unknown Alternate Universe eerily similar to his own, Harry finds some measure of solace:
Hell's bells. Even the whole WORLD was nearly exactly identical to my world. The languages, the cultures, all of it the same. I even found a copy of both Star Wars and Star Trek here. At least I was someplace civilized.
Harry acting as a complete smartass to Sona at the beginning of the story. It's just the way how he is both tiredly resigned to the Student Council President's nagging and very much looking forward to mouth off to her.
Sona: Dresden-kun, if you have a moment, there is something I'd like to speak to you about. Harry: Ah, Sona! How have you been? My, you're looking quite lovely today? Is that a new brand of make up? The way it makes your eyes flash… Sona: I do not wear makeup. Also, please address me by my appropriate title of "Kaichou". Harry: Of course, of course, Sona. So, what can I do for you on this fine day? A movie and a dinner out? Maybe a walk in the park? Or perhaps something more romantic? Sona: Dresden-kun, I am not, nor ever will be, interested in you romantically. Please refrain from making such implication in the future. Harry: Ah, but you look so cute when you're angry. Your eyes get all flinty and your button nose gets all scrunchy. Like a little puppy… Tsubaki: Why you…! Sona: Control yourself, Tsubaki. The provocations of misanthropes shouldn't be risen to. Harry: Ohhh. Misanthrope. Sorry, that's such a big word. Can we tone it down a bit so I can follow the conversation? Sona: Misanthrope: one who is a troublemaker or fails to conform to social conventions. As in you, Dresden-kun. Harry: Ah, shucks, thanks Sona!
Raynare: You… You dare? You dare raise hands against me, you human? Harry:Of course. You see, as a card carrying member of the human race, I, naturally, have to take exception to seeing one of my own being attacked. [beat] And it was a staff. Raynare: What? Harry: I "raised staff against you." What can I say? Walk around like that and of course you're going to give someone wood. Raynare: Impudent dog!
Harry's recurrent and petulant indignation that only Devils find his jokes funny.
Harry getting a taste of what it feels like to explain things to someone just clued into The Masquerade when Issei tells him about the Riser mess. After he gets the full story, he's rather pleasantly surprised that for once, he didn't get sucked into things.
Issei's Skewed Priorities when Harry gives him the Cliff's Notes of hosting a supernatural entity in his own person after he learns about Draig.
Issei: Wait. You keep saying "she". Harry: Yeah, [Lash]'s a woman. Issei:[beat] …How big are her oppai? Harry: Pardon? Issei: Her oppai. Are they big? And can you touch them? Asia:[pinches Issei's cheek] Harry:[facepalms and sighs] Actually, yes. To both questions. [Issei and Asia freeze at his words] Harry: I did mention she could make me feel things that weren't there, didn't I? Also, she's smoking hot. Issei:[begins crying] Ooooh! Why! Why do you have a gorgeous spirit with oppai that you can touch and I have this stupid dragon! Why! Why is the world so unfair!
And the punchline, where Harry makes Issei believe Lash is standing right beside them, prompting the breast-loving guy to try to grope her because he completely missed the point that Lash basically manifests herself as a hallucination. Plus Asia desperately trying to keep him from doing it, even offering to let her crush feel her breasts instead. Even Lash herself found their antics Actually Pretty Funny despite normally not liking him describing her doing things that she isn't.
Previously in the same scene, Harry tells Issei and Asia about the "voice in his head" and her current cosplay hobby. Asia immediately pulls out her Sacred Gear and tries to heal Harry's head while swearing to "heal whatever is wrong with him!" Treating Harry as an obviously insane person like this would have been a perfect Deadpan Snarker response except that Asia actually means it. Even Harry could do nothing but thanking her good intentions and then further explain that Lash is really her own person.
Earlier, when Issei asked for advice for dealing with a voice in one's head, Harry great pleasure in leaving before Sona can get any context to what the heck is going on.
Almost every time Harry interacts with Asia, he has to fight down the urge to "buy her ponies, dolls, lacy and frilly dresses, and all manners of cute stuffed animals." He finds her just that nice and adorable.
Also, whenever Asia puts on a determined face, it's described as "that war face of hers that menaced balls of yarn everywhere" or something similar.
Harry dubbing the holy swords forged from the broken pieces of the original Excalibur the "Excalibits," and how the term catches on. Especially Koneko's incredulity whenever someone new just goes along with it.
When Kiba tells about his Dark and Troubled Past to the group, Issei decides they all should share something of themselves with the others. What should have been a Heartwarming Moment takes a turn for the cringe-worthy when Saji tells them about his dream of getting Sona pregnant and marrying her, and Issei's about groping Rias and sucking on her breast. Then it takes a turn back to funny when Harry looks at Kiba and Koneko and incredulously asks them if that sounded as creepy to them as it sounded to him, at the same time Issei and Saji actually bond over their disturbing/perverted life goals.
Harry: And the crescendo of creepiness continues…
There's a moment in that scene where Saji sees the silver lining in the fact that Sona is interested in Harry. Namely the confirmation that she at least "isn't attracted to good looking guys like Kiba," meaning that there's some hope for him. You would expect Harry to retort to that, but he merely thinks of Thomas and admits to himself he never was the good looking one in the family.
Harry punching Freed Sellzen in the face. It's just his childish joy at it what sells the moment.
Nobody ever expects the wizard to get physical. Seriously. It was great.
The DxD canon Comedic Spanking punishment scene is all the funnier for Harry's presence.
Harry pondering that if Mab had similar disciplinary measures, it'd have made working for her a lot less nerve-wracking.
When Saji tries to get Harry punished too, Dresden very maturely tells Sona "you aren't the boss of me."
Harry having to fight the bromanticism again when Issei realizes why he recorded Saji hiring him to help the group, and Saji's relief when Harry cuts off before the tape gets to the point where he revealed the dream he mentions above.
Minutes later Sona, also very maturely, kicks him on the shin for endangering himself and then she tries to convince him he just imagined it. In the background Rias is barely keeping herself from giggling at their interplay because she still needs to maintain a straight face in order to scold her Peerage.
When Ise gives Harry a look begging for help when Rias begins to spank him, Harry tries to give him some solace — emphasis on "tries":
Harry: Er. You know, there are places where you have to pay for that kind of thing. Issei: Ehhhh!
Harry having to dress and act as a Japanese Delinquent now that he can't do his stakeouts discreetly from a car. Bonus point for worrying that Sona would never let him live it down if she sees him like that.
Harry:[grumbling to himself] Embrace the clichè, Dresden. Use the clichè, and make it your power. Who needs a good reputation anyway? Bah. Stupid things, good reputations. Never had any use for them.
Harry fighting against the Bromanticism:
Harry:[to Issei] Okay, seriously. We're guys. We're not allowed to admit we have emotions. It's against the man code. Let's quit with the heart to heart mushy stuff, grunt, and pretend like that last bit never happened, okay?
Harry and Lash's reaction when Issei actually stops and considers Kokabiel's offer to join him in exchange of a harem of beautiful women.
Harry:[groans] Well, it's a good thing the Denarii don't exist here. Because if they did, Ise wouldn't last a week. Lash: Some things are just too easy. Rias: Geez! Ise! Stop drooling!
Sona and Harry's banter when he gives The Summation of the battle against Kokabiel and co. to the Student Council.
Tsubaki: Frenemy? First Excalibits, now frenemy? Harry: Hey now, I didn't make up that word. I can't take credit for every awesome phrase that pops up, right? [beat] Or can I? Hmmmm… Sona: Perjury is a crime, as is copyright infringement. Harry: Why have you declared all fun your enemy, Sona? Did fun do something to you in the past? What is the source of this crusade? Sona: I have fun. It's just my definition of fun involves far less rampant violation of rules, courtesy, common sense, and decorum. Harry: I'm trying to equate the definition you just provided to any objective definition of the word we're talking about. So far, I'm having trouble finding any matches. [yelps][incredulous] Did you just stomp on my foot? Sona:No, that would be ridiculous. Momo: Kaichou always looks like she has so much fun when she's flirting with Dresden-kun. Ruruko: They make such a cute couple. Tsubaki: Now, now. None of that, you two. Saji: Hmph.
Harry:How long were you there? Tsubaki: Er, Whatever it is you and Lash get up to at home, I don't think school is appropriate for MaidNaked Apronplay. And should you really be doing such things when Kaichou has already confessed her feelings to you? Harry:[groans] God, kill me now. Lash:[laughs]God is dead, my host. Harry: I hate Bizzaro World so much.
A few scenes later it is revealed just why Lash did all that when Harry opens the door of the Student Council office.
Tsubasa:[grinning] Welcome back, Master. Harry:[without missing a beat] Sorry, wrong room. [closes door] Issei: Hey! What do you mean wrong room? It says "Student Council" right on the door. Harry: That must be a mistake. Because there's no way that half the Student Council would suddenly decide to wear maid costumes. That would be ridiculous. There was no way that Sona or Tsubaki would let something like that happen: she'd be too busy stomping everyone back into their proper uniforms, rather than sniffing… [opens door] Tsubasa:[still grinning] Welcome back, Master, Harry:[to Sona and Rias] Why are you sniffing my coat?
On the "sniffing Harry's confiscated coat" bit, it turns out Sona didn't notice the enchantments Harry had cast on his duster until Rias pointed it out, and they were trying to figure out what the spells were by holding his coat closer to themselves. Of course, that wasn't what it looked like to him at first.
Sona: Perhaps because she is less familiar with you, Dresden-kun, but Rias happened to take notice of something that I had overlooked. Harry: The fact that I wash my coat lining regularly? The type of cologne I use? My favorite brand of leather lotion? My manly musk? Reya: Dresden-kun!
I wasn't certain which of the members of Sona's peerage had been the one to start the rumors, or if they had done it on purpose, but apparently the day after I had had my pow-wow with them it had been a popular gossip that the three of us were in some kind of love triangle. It had taken a day after for it to be common knowledge that I was leading them on, and the next day it was established fact that I was cruelly taking advantage of two innocent girls while engaging them in depraved sex acts. Hell's bells, these people needed hobbies.
Georg calling his teammates out for attacking Harry when they were supposed to be trying to pitch to him why he should join them.
Harry and Georg both dislike Harry Potter, and it seems that most other magicians don't either. Apparently, there's been at least one attempt to have a devil make a contract to take out a hit on Rowling, with Mephisto himself having to turn it down.
Harry's first meeting with Sirzechs on Family Day. Sona is hesitant to introduce them because she knows how Harry is like around authority figures, but then he goes against her expectations and shakes his hand with never-seen-before politeness. Sona simply couldn't believe Harry could actually behave himself and that showed clearly on her face.
Sirzechs proving to be more than a match for Harry's smartassery and Pop-Cultured Badass-itude. Harry never saw it coming.
Sirzechs: Rehab? So the glove isn't just for show? What happened? Harry: Vampire with a flamethrower. Sirzechs: It was Tuesday, wasn't it. I know whenever I come across a vampire with a flamethrower, it's always a Tuesday. Harry: Oh, you're good. You're very good. I won't go down without a fight though. Lord Gremory: What a lively young man.
Serafall: Ne, ne, Sirzechs-chan. Is this boy the rumored dragon…? [trails off as she notices Harry] You! Harry:[points a finger at himself] Me? Serafall: You! [points dramatically at him] You're the one that's trying to take away my So-tan! Harry:[cleans his ear with his pinky finger] I beg your pardon? Serafall: Don't act like you don't know! The other day, I found where my So-tan was hiding her dating magazines! My cute So-tan can't be reading love manuals! And she even asked our mother for love-love advice instead of me! How can my So-tan be so rebellious! Saji: M-manuals! Sona:[blushes madly in mortification] Serafall: My cute Sona-chan who used to follow me around saying "Onee-sama, onee-saaaaama!" is too young to be dating! She should still be running up to me while saying that and I'm saying, "Sooooo-taaaan!" before we embrace in a yuri-yuri way! [points her prop stick at him] Don't think for a second that Magical Girl Miracle Levi-tan will let you steal away her So-tan!
Harry's narration to all of the above:
Okay, I was of two distinct minds about this development. On one hand, this was the Leviathan, one of the four rulers of devils, who probably wouldn't lose out in power to what I felt from Sirzechs before, and she was currently proclaiming an enmity to me that was probably one of the most serious dangers I have come across since I made it to Bizzaro World. On the other hand, it was a cute short girl in a cosplay outfit pointing a stick at me. I was beginning to suspect that logic didn't hold much sway at this place and moment in time.
Harry and Serafall finding some common ground in the fact they like to do their jobs in their own, unique ways. And other people's reactions to their sudden rapport.
Harry: I like your outfit. Serafall: Really? Harry: Really. It gets so old when all the super powerful demons and monsters always seem to have to wear fancy armor or dramatic robes, or even just super expensive suits and stuff. It's nice to see someone in your position willing to buck tradition and strike out for something more unconventional. Sirzechs:[a bit uncomfortable] Aha. Serafall: Oh, I know! But no one ever seems to agree with me! All the other devils are always like "show more dignity" or "you're going to embarrass us if you go out like that"! Don't they understand that I'm really into Mahou Shoujos right now? Harry: I know just how you feel. I get it all the time too. People are always saying "why don't you wear a robe instead of that coat" or "what kind of wizard just shoots someone". It's the twenty first century people. Just because you never really trusted indoor plumbing because it's only been around for a century or two doesn't mean I have to pass up on it. Serafall: I know, I know, right? I can shape my magic however I want it, so if I want to shoot twinkling stars, it's not like it's hurting them or anything! And what's wrong with striking a pose and giving a speech about love and justice before a fight? It's so much cuter than those long drawn out dramatic speeches about how you're going to crush your enemy! Harry: Oh god, I get so sick of those. After a while they all start sounding the same. And why should I waste magical power to make a fireball when I can just use a shotgun with Dragon Breath rounds? I mean, it'll burn the building down one way or the other, so who cares if it comes from my staff or my firearm? Saji: Is he still trying to get guns? Issei: Wait, doesn't it sound like he's already shot people in the past like that? Rias: This far exceeds even my most outlandish speculations.
When Harry and Serafall eventually clarify that they think that you shouldn't begrudge someone if they try to do a job their own way (as justification for their respective outfits defying the usual social tropes regarding their jobs), Sirzechs takes this to heart, mentioning that he has always been a fan of Sentai teams.
Harry complaining to Sona and her Peerage about the times (notice the plural) he got home and found his brother Thomas in the middle of A Party, Also Known as an Orgy. He meant it simply as an anecdote, forgetting for a moment that he hangs out mostly with teenagers now. End result: a roomful of very red faces, a too-curious Tsubasa asking him if he ever joined them, and an angry Sona seconding that question.
Harry asking Azazel to answer for his crimes against man-kind:
Harry: I meant for having invented make up, hair care, and jewelry. Azazel:[blinks in confusion] Harry: I mean, you are the Fallen responsible for teaching mortals about cosmetics, aren't you? Do you have any idea how many men have suffered having to go around with their girlfriends and wives and pretend that they really saw a difference between two identical brands of hair dye? Sona:[hissing] Dresden! Azazel:[realization hits as he slowly begins to laugh]Haha! A follower of the classics! The Book of Enoch?
Harry's complete bafflement at Gasper's Forbidden Balor View and the sheer amount of Required Secondary Powers for something like a Time Stands Still power to even work like it does. Plus Sona's amusement to said bafflement.
Sona: You said you knew what you did wrong [with the Calculated Spell]? Harry: I tried to micromanage. I'm too used to handling all the parts of the spell that when I tried to activate this one I was riding the spell worse than you ride your Peerage. Sona: I will have you know that I do not micromanage. I administer with prejudice. Harry:[disbelieving] Did you… did you just make a joke? Sona:[tries to change the subject] So if you spent too much effort attempting to control the spell, why was the effect so contained? Harry: Because I'm more used to using circles for defense… and you DID make a joke! My god! This has to be some sort of special event! I wouldn't be surprised if a holiday was named for today! Maybe I should call Levi-tan so she can-ow! Sona:[pretends she just didn't kick him in the shin] You should be more careful. There are still many falling rocks. If another were to hit your leg like that we might require Asia-san to treat you again. Asia: Ahhhh, but wasn't that Kaichou… eep! [scrunches herself to present a lower profile when she notices the look Sona was giving her] Harry:[to Sona] Shame on you, bullying a little girl like that.
Later on the same day, Harry finally has it with the Double Standard: Abuse, Female on MaleSlapstick Comedy and retaliates Sona's mistreatment of his cheeks by messing up her hairdo. This devolves into a childish "you let go first" kinda fight that ends up with the two falling to the ground, one on top of the other. They look at each other and get very close to just go ahead and start kissing until they suddenly remember they've got an audience. Then they get up, badly pretend nothing just happened, and hastily say their goodbyes and leave in opposite directions.
Lash tongue-in-cheek assuring Harry that the real reason why most dubious organizations try to recruit him is because his height and an "appropriately malicious attire" would help cowering their enemies.
When Harry calls Georg a stalker and complains aloud that he never gets what he calls "the good kind of stalker" — namely a "hot, overeager, sexually aggressive cheerleader" — Siegfried teasingly asks Jeanne whether she would put on a cheerleader uniform to sway Harry in their favor. She refuses, but Harry points out that she only objected the last qualifier, which he says perked up his interests. Jeanne catches the implication and blushes.
Harry making his escape (literally!) from Dimension Lost' Pocket Dimension while making sure the last thing the Hero Faction sees of him is his raised middle finger as he closes the portal behind him. Doubles as a Moment of Awesome that tells you everything you need to know about Harry Dresden in a single frame.
Beyond the Outer Gate Lies... a High School Library?
Lash treating the girls that are becoming interested in Harry as a competition with Issei when Reya starts showing an attraction to him.
Harry's reaction to realizing that the real Thor plays him in the MCU.
The meta-humor of Harry saying that if he ever had his life story written down, he'd have Jim Butcher do it.
The Perverted Duo spicing up the rumors about Harry's Urban Legend Love Life by saying he used Mind Control magic to bring Reya into his brainwashed harem that already included Sona and Tsubasa, and forcing them all into Black Magic-themed ritualistic orgies. The kicker is Asia earnestly defending Harry and assuring everybody who would listen that Harry would never user Mind Control magic and... that's it. That's really the extend of her defense. It seems the sweet and adorable former nun does find the idea of the four them having orgies for fun and magic-related purposed to be at least plausible.
When Harry's threats of turning the Duo into toads just gets them thinking about how to use that to perv on girls, he uses a calculated spell to make them smell like burnt yak hair.
Harry dubs the Beholder leader in Kuoh "BB", short for "Boss Beholder" or "Beach Ball". Argus later decides that he likes the name and makes it official, much to BB's frustration. At one point he asks for an explanation on the nickname for another Beholder in the hopes that it'll be worse than his own nickname.
Harry managing to get confirmation of the Hero Faction's intentions towards Alice, because Heracle's poker face is just that bad.
The way Jeanne described Sona and Serafall to Alice.
Alice White: [Jeanne] told me [Harry Dresden] was handsome, in a scary way. And he was supposed to be with a smaller girl… She said if that girl was flat as a board, her name was Sona Sitri, and if the girl had huge, fake looking… um breasts… that her name was Serafall. Sona:[frowns]
The whole Running Gag with Harry's In-Universe character "Wandering Wizard"/"Mercenary Magician" having a hat while Harry doesn't.
Georg has a female Hero interested in him, who tries to eliminate Harry in a (platonic?) Murder the Hypotenuse scenario, even calling him "incubus".
Later, her name is revealed to be Circe, and when Georg admits his interests are more along Jeanne's type, she's eavesdropping and taking notes.
Sun Wukong dropping the Yasaka rescue team in the middle of a crowd of tourists on purpose after the Heroes bail and they need to escape the now crumbling pocket dimension.
Oakley managing to inject her Texas accent back into her speech patterns even through Language through sheer will and pride.
When Bizarro!Mab requests Harry's presence for negotiations with the Devils, Harry is prepared for meeting a Magnificent Bitch as his Mab was... and it turns out that this Mab is The Ditz. Lash spent the entire night laughing about it.
Plus, how they convince Mab to accept the deal: offer to play As Herself in Miracle Levi-tan.
Sona and Serafall's father tries to get Harry to stop seeing his daughters, even offering him immortality and unique magical books. Unfortunately, he wasn't paying attention and his wife and said daughters heard him. By the time his wife is done with him, he looks like a Bandage Mummy.
Kendra is rather frazzled after shopping with Akeno.
Harry pranks Kendra by dying her whole body pink, forgetting that the spell he was going to use to undo it needs him to scrub the target area vigorously. He decides to blame Lash.
When Saji realized that Azazel might give him a character in "Miracle Levi-tan" and/or "Oppai Dragon", he actually leaps away to avoid it.
Cao Cao, Sieg, and Heracles actually like their Psycho Rangers depiction because they're big fans of the franchise and had actors that played Rangers previously depicting them, and even debate on whether or the acting choices were the best.
When Dresden calls out how the rules of an upcoming Rating Game give Sona's team an unfair disadvantage despite seeming fair at first glance, he pretends to be a reporter, calling himself "Clark Kent" from the "Daily Bugle", with many of the actual reporters getting the references.
Duncan tries to split Harry and Sona up again, this time by using Sona's statement that she wouldn't marry a man who couldn't beat her in a game of chess. Not only is what he's doing extremely obvious to them, they manage to circumvent it without issue by Sona just letting Harry win (with a bit of help from Lash).
Harry and Lash's incredulity at meeting the Dx D world's Hades, being used to the more amicable one from their own world.
Duncan's sister, just out of the blue, asking Harry if he could father her children.