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favorite and least favorite gym leader from each gen?

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what the title says. you can explain your reasoning if you want, but you don't have to.
here are my personal picks:

gen i
  • favorite: blue, but if we're talking strictly kanto-focused games then sabrina. erika is a very close runner up though.
  • least favorite: brock i guess, he's just not particularly interesting to me compared to the others.

gen ii
  • favorite: jasmine (unsurprisingly), she's adorable and has such a lovely and kind personality. (plus, well... amphy!)
  • least favorite: clair. maybe whitney isn't a great sport, but at least she didn't send you off on a fetch quest (that can potentially soft-lock your game in gs) in order to actually receive the badge.

gen iii
  • favorite: wallace and winona a million times over
  • least favorite: wattson, i don't dislike him but he's not nearly as standout to me as the rest.

gen iv
  • favorite: roark. not sure why lol, i just like his vibe.
  • least favorite: crasher wake, i can't bring myself to care about him at all, sorry...

gen v
  • favorite: probably elesa or roxie, i can't really pick
  • least favorite: cress i suppose, he's just a little too smarmy for my liking.

gen vi
  • favorite: valerie. adore her otherworldly design and unique personality... and her ace is my favorite pokemon of all time which may help lol
  • least favorite: i honestly like all of the kalos leaders to some extent, ramos just sticks out the least in my head

gen viii
  • favorite: bea for sure, love her design and general vibes. great mix of cute and badass.
  • least favorite: melony simply on the grounds that she pressure(d? s?) gordie into continuing using the ice type instead of pursuing his own favorite. she's fine otherwise, that just irks me a lil d: let the kid do what he wants, he ain't hurting anyone!

gen ix
  • favorite: larry and iono (obvious reasons are obvious)
  • least favorite: kofu, i do not find him interesting at all. i also do not care much for his physical design, it is just uncanny to me. other than him paldea has my favorite gym leaders in the series, so :sadsola:
 
This is a tough one.

Gen I

Favorite: Sabrina
Least favorite: Blaine

Gen II

Favorite: Falkner
Least favorite: Chuck

Gen III

Favorite: Roxanne/Winona tied
Least Favorite: Juan

Gen IV

Favorite: Volkner
Least Favorite: Crasher Wake

Gen V

Favorite: Elesa
Least favorite: Burgh

Gen VI

Favorite: Clemont
Least favorite: Ramos

Gen VIII

Favorite: Bede
Least Favorite: Piers

Gen IX

Favorite: Tulip (I’d peak Iono if it wasn’t for the sharp teeth)
Least Favorite: Kofu
 
Kind of hard for me as my favorites sometimes flip-flops often, and depends on replays and/or my mood towards them that time.

Gen I
Favorite:
Lt. Surge, though Brock and Misty are pretty high up still in my favorites from this gen.
Least favorite: None really, I used to dislike Erika but that was mostly from the anime and mainly her gym trainers that soured me on her; now though, I don't really dislike any this gen, mostly indifferent to the others.

Gen II
Favorite:
Morty, his design is so handsome imo. Falkner and Clair are pretty great too.
Least favorite: Chuck, he's really mediocre imo.

Gen III
Favorite:
Tie between Norman and Juan. The former he's the MC's dad, and that's cool in my book; the latter I just really like him design wise the most. Both are also quite handsome too.
Least favorite: Tie between Wallace and Wattson. I used to like the former, but Juan is a better Sootopolis gym leader imo, plus I'm not a fan of his ORAS design lol; the latter he's just very, very mediocre also.

Gen IV
Favorite:
Fantina, her design is so pretty, and I love her purple hair and dress; her badge design is also really cool. Roark and Volkner are also my favorites after her.
Least favorite: Eh, maybe Crasher Wake. I don't really dislike him much, but I'm not fond of his design tbh.

Gen V
Favorite:
Five way tie between Lenora, Clay, Drayden, Cheren, and Marlon. They're all just so great design wise, but if I had to pick one, then Drayden.
Least favorite: Burgh, he's just been meh for me lately.

Gen VI
Favorite:
Olympia, she has a pretty design and it makes her look so wise imo.
Least favorite: Ramos and Viola, they are two I forget about the most in this gen.

Gen VIII
Favorite:
Three way tie between Bede, Kabu, and Raihan. But I'd say Bede as my top favorite because he's so smug and such a jerk at first lol.
Least favorite: Piers, I thought I'd like him because his design is neat, but he just fell short unfortunately.

Gen IX
Favorite:
Three way tie between Iono, Larry, and Grusha. Iono and Grusha have great designs, but Larry actually feels (and is) more realistic, so I'd have to say him for my top favorite this gen.
Least favorite: Kofu, just not a fan of his design personally.
 
Gen I

Favorite: Blaine(cause of the manga)
Least favorite: Erika

Gen II

Favorite: Whitney and Claire
Least favorite: Pryce

Gen III

Favorite: Norman and Flannery
Least Favorite: Juan

Gen IV

Favorite: Volkner
Least Favorite: Crasher Wake

Gen V

Favorite: Elesa
Least favorite: Burgh

Gen VI

Favorite: Korrina
Least favorite: Ramos

Gen VIII

Favorite: Raihan
Least Favorite: Opal

Gen IX

Favorite: Ryme(She was surprisingly tough)
Least Favorite: Larry(No emotions)
 
It takes a while to I find it, but I was sure I had already answered the question raised by this thread years ago. Well, here's my answer (I don't think my opinion has changed much):

It is a difficult question. Of course, there are always those characters with whom we identify, be it by the pokemons they use, by the personality they display, the structure of their gyms, the challenge they provide or any other reason. That said, I don't remember to really dislike any gym leader and this is the most difficult part. But, let's go try.


Favourites:
Kanto:
Brock or Misty, they are so relevant to the franchise that is hard don't choose one of them. Nice characters, anyway.
Johto: Whitney, Silver was the first Pokémon game that I played and the normal gym leader was a real pain in my ass. Then, when I finally defeated her, the pretty and wrong-headed girl starts to sob !? Come on, Whitney!! You know how much I suffered too. Honorable mention: Clair and Falkner
Hoenn: Wattson, he is always in a very good mood. Looks like a funny little old chap.
Sinnoh: Volkner or Candice. The first one has a cool design and a sore mood, strong empathy here. The last one is a quirky girl with peculiar habits like talking in third person. I enjoy her quotes and her interactions with Maylene.
Unova: I vouch for Iris in BW and Roxie in BW2. While I dislike Iris in Pokémon anime, the game counterpart save the character for me. I was very happy to see Iris achieve her dreams as a real dragon trainer and become the Champion. Plus, a very nice participation in Pokémon Generations. In her turn, Roxie has a amazing characterization and a toxic song.
Kalos: Korrina, she has a awesome mega-evolution and a very enthusiastic personality, plus she has a more active role in the anime. Besides that, she gives away a Lucario (with the respective mega-stone) of her own to the protagonist. Is there a better gift? Maybe only a kiss of her own. Lol
Galar: Tough one. Bea, she exudes determination, focus, effort and commitment. Serious, when I gym battle against her I wished she could win, looks too wrong beat her :X3:. Honorable mentions: the old grannie (Opal) and Piers.


Least Favourites:
Kanto:
While I like Giovanni, I don't think that he added something as gym leader.
Johto: I don't know, I like them all. Maybe Bugsy or Morty?? They seem the more simpleton.
Hoenn: Brawly, he has very little interactions and no feature that stands out. Obs: I very like Tate and Liza, but their team is ridiculous. Serious, they are the seventh gym leaders and each other has only one Pokémon...
Sinnoh: Roark, simple and generic design. He hasn't a really great feature, the better one is that he has a whole family in game, being Byron, another Sinnoh gym leader, his father.
Unova: I really don't know, all are alright and unique. Maybe Burgh, not much role despite being the leader of the biggest city.
Kalos: Ramos, I think that he should retire. He has a pleasant personality, but has no thrill. I would rather have a warm tea with than battle against him. And I also believe that he prefers the same.
Galar: Gordie, he is quite presumptous and a little snob. His mother looks nicer than him and match better to the theme and environment of Circhester Town.

Well I think I just have to add Paldea's one:

Favourite: Larry, a very unexpected, relatable and refreshing character, I would like to know more about him. Honorable Mention: Brassius! What an incredible design and characterization, the best of the franchise along with Roxie.

Least Favourite: Iono....I am just sick from Youtube and Tiktok, duh.

Addendum: My least favorite Johto leader is Morty. It's not that I have anything against the character, but, as the Gengar trainer and the leader of Johto's most lore-rich city, he should just need be more than simply "handsome".
 
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Kanto:
  • Favorite: Sabrina. I like her design and the characterization she gets in later games about working to be more sociable. Honorable mention to Lt. Surge for using my favorite Pokemon of all time, Kantonian Raichu!
  • Least Favorite: I don’t dislike any of them, but Erika’s the one I’m the most “indifferent” to.

Johto:
  • Favorite: Clair. This may just be Masters characterization factoring into my decision here, but it is interesting to see how her relationship with Lance impacts her as a Gym Leader and as a person.
  • Least Favorite: I dunno, Chuck? Same situation as with Kanto’s least favorite.

Hoenn:
  • Favorite: Wattson. He mains my favorite type, has intrigue from his involvement with New & Sea Mauville, and is just jolly! Honorable mention to Wallace for… Wallace in general, actually.
  • Least Favorite: Skip :)
In all seriousness though, Juan, if I HAD to choose. I still like him though.

Sinnoh:
  • Favorite: Volkner. He mains Electric, and he has Raichu. Enough said.
  • Least Favorite: Fantina, solely because of her gym puzzle being dark and forcing me to squint to see the symbols on the floor in Platinum.

Unova:
  • Favorite: Cheren! He is literally my pfp, of course I had to choose him here. I really like him as a character, and as a Gym Leader he’s no slouch for a first challenge either!
  • Least Favorite: Marlon? This was another tough one, as I like all the Unovan leaders. However, Marlon’s gym battle was a little too easy for my liking (in Challenge Mode).

Kalos:
  • Favorite: I’ll give Korinna and Wulfric respect for doing things outside their gyms (Korinna had the whole Successor thing, and Wulfric checked on Pokemon Village). None of the battles are anything noteworthy, and all the puzzles are solid but not standout IMO.
  • Least Favorite: Valerie, only because IIRC she has a Mawile on her team, serving as a constant reminder of what could have been if Game Freak let more NPCs use Mega Evolution.

Galar:
  • Favorite: Piers! Close race between him, Opal, and Raihan. They all rock, but Piers felt really unique in SwSh for his banger of a battle theme, his gym’s lack of a Power Spot, and just being the first Dark-type gym leader in the main series!
  • Least Favorite: Milo, I guess? He’s unremarkable to me, but I suspect that’s because his battle and his gym puzzle were intentionally easy as a first gym.

Paldea:
- I didn’t play SV.
 
Gen 1
Favorite: Sabrina/Brick (im not fixing that)
I love Sabrinas fits she always looks so cool, and Brock is mainly because the anime, 10/10 Ash's best traveling buddy.
Least Favorite: Idk probably Blaine hes boring

Gen 2
Favorite: Clair, pretty lady.. Also she looks cool and uses dragons
Least Favorite: Pryce, hes a dumb boring old man.

Gen 3
Favorite: Whoever the flying leader was im forgetting her name atm, I just really liked her design and her team was interesting. Also she's in the best city in all of Watson

Least Favorite: Watson I just dont like the guy.

Gen 4
Favorite: Byron or Volkner. I loved Byron in the anime, and I think its cool he uses the opposite fossil to his son. I like Volkner because he looks cool, also his match with Ash in journeys was amazing.

Least favorite:Crasher Wake I do not like his design, HOWEVER i like how cracked his rematch team was in BDSP

Gen 5
Favorite: Roxie or Drayden. I want Roxies guitar, also her ace is the best Unovan bug type besides Leavanny. Drayden, ..its Drayden idk what else you want me to say.

Least Favorite: Marlon hes boring as hell.

Gen 6
Favorite: It has to be Korrina, I loved her arc in the XY anime, (I also ship her with Bea). Korrina's actually my favorite gym leader, it'd be weird to not have her as my favorite. I might make her my profile...

Least Favorite: I don't have one because im extremely in different to the rest of them in the games (besides Korrina) or like them in the anime. Uhh Ramos?

Gen 7:
Favorite: If the Kahunas are the gym leaders then I like them all especially Hapu.

Gen 8
Favorite: Bea, her Twilight wings episode is probably my favorite in that web series and I ship her with Korrina. Oh, i also love her rivalry with Ash in Journeys

Least Favorite: Gordie??? he just doesnt do anything for me

Gen 9
Favorite: Larry, Larry.

Least favorite: Uhh the water guy i dont fw him all that much.

(Quick edit, shoutout to Jasmine, Giovanni, Kabu and Iono, oh and Cheren)
 
Gen 1

Favorite: Giovanni
I think the twist involving him is still great. Walking by the gym early adds to the mystery. I also love his backstory with Silver in HGSS.

Least favorite: maybe Misty?
I really don't like how they portrayed her in Gen 2. Why is she mad at the protagonist because her date left? That is like yelling at a stranger on the street about your personal problems lol.

Gen 2

Favorite: Jasmine
Her story is cute and sad! I like her lolita inspired contest outfit in BDSP too.

Least favorite: Whitney
She is kind of annoying and you hate her but it's also a good kind of hate? She has cute Pokemon but is super toxic, it's a funny contrast lol. Claire is also annoying but she just has a really cool vibe to her with her cape and dragons that Whitney doesn't have.

Gen 3

Favorite: Watson
He is a character with hidden depths! He is this random old man who has the most epic past lol. I love stuff like this in games.

Least favourite: Roxanne
She is very forgettable tbh. Easy fight as well.

Gen 4

Favorite: Volkner
I love his relationship with Flint and his depression arc.

Least favorite: Candice
Hate her designs, ugh that brown skirt... The town is snowy and cozy so her vibe is totally off.

Gen 5

Favorite: Elesa
Love her interactions with Bianca and the Utada Hikaru song in BW2! I also ship her with Emmet. I have a complicated headcanon that there was a love triangle between her and the twins lol.

Least favorite: Cilan
I loved the Shadow Triad theory back in the day. When it was debunked I never recovered lol.

Gen 6

Favorite: Wulfric
Awesome in the anime and I love how he has a little village with Pokemon that were hurt by humans. Interesting how he has an Ainu name (Urup) in the Japanese version too.

Least favorite: Valerie
Ugh, those eyes...

Gen 8

Favorite: Opal
I love her relationship with Bede! Super wholesome old lady who is a little crazy.

Least favorite: Milo
Ugly design tbh...

Gen 9

Favorite: Larry
Love the memes. Tired office worker.

Least favorite: Katy
Bug type gym leader who makes cakes? Idk that is a little gross...
 
I
FAVORITE: Either Erika or Sabrina. Erika has very serene personality and pretty design that I vibe with. Meanwhile Sabrina is badass and I like the eerieness about her. Honorable mention to Lt. Surge. Man is straight up Guile, and I think that's funny.

LEAST:
Koga. Idk, man just doesn't have as much personally compared to the rest.

II
FAVORITE: Clair. Extremely cool design, and I think it's funny that she initially comes off as cool and reserved but can also be a bit of a sore loser. I know that makes her controversial to some, but to me it puts a lot of realism to her and I think it's a fun angle.

LEAST: Bugsy. I'd say half of the Johto leaders admittedly don't do much for me and admittedly feel a bit half baked. Bugsy in particular is very generic with neither a cool personality or design to really leave an impact on me.

III
FAVORITE: Norman. Your dad not only being an actual character, but also being a gym leader? Way too cool!

LEAST: hmmmmm... Watson???? I don't feel as strong about this compared to others here, but the other gym leaders of hoenn just leave a stronger impression for me. Also his original and remake ace being a non gen III mon is perplexing.

IV
FAVORITE: Either Gardenia or Volkner l think. I'm admittedly not that strong about any of the Sinnoh leaders, but these two have really fun and iconic designs.

LEAST: Rowark. Just very boring and not really that standout to me.

V
FAVORITE: Skyla. I mentioned this a couple months ago but I really love her bright blue/red color aesthetic. Also her gym is pretty fun and memorable.

LEAST: Marlon. Very boring. He's so boring I don't have much to write up about him here

VI
FAVORITE: Either Valerie or Olympia. Valerie is very elegant and her desire to be a pokemon strikes me as a pretty easy (and I assume accidental) proxy for being trans, so I can easily relate to her. Meanwhile Olympia has a cool and mysterious design, whilst her ace is my single favorite Pokemon

LEAST: Wulfric maybe? He's so basic and forgettable for me.

VII (Screw it, I'm rating the Captains and Kahunas too)
FAVORITE: For Captain, Mina. Love her design, aesthetic and personality.

Nanu for Kahuna, I like his vibe and was our first major Dark specialist that wasn't E4, so that's extra points there

LEAST: Lana or Sophocles for captain. Again don't feel that strong about em, they're just not as memorable compared to the other captains.

Hapu for Kahuna. Don't feel that strongly about her, just not as good as the other ones yada yada yada.

VIII
FAVORITE: Does Klara count? If not? Bea. Real fun design and general aesthetic. She kinda gives me Min Min ARMS energy.

LEAST: Milo. Ya know, basically all the other Galar Gym Leaders are actually really fun and memorable. Milo on the other hand is pretty bland and weirds me out.

IX
FAVORITE: Larry. I've expressed my appreciation for Larry multiple times, but office worker normal leader was just a genius concept with a great execution.

LEAST: Brassius. Feel like he's a bit underdeveloped in both design and character. He ain't even bad, but he gets vastly outshined by the other Paldea leaders.
 
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Kanto:
Favorite- Erika. I dunno. She seems chill. Plus her gym's cool.
Least Favorite- Lt. Surge. Lemme get this straight, son. First you put up a cut bush to keep people out. But you ALSO have a shitty electrical button trashcan puzzle? Do you want to be a gym leader or do you want to be a paranoid little biscuit?

Johto:
Favorite- Morty. This man is cute.
Least Favorite- Whitney and Clair for being unprofessional lil bitches.

Hoenn:
Favorite- Wallace. This man is king cute.
Least Favorite- Tate and Liza. I'm sorry. Did you two little beans get confused? You're not the first gym. I you're the second to last. I should not be able to utterly curbstomp you with one pokemon using surf. In a double battle. Because you both know we'll have surf because it's the only way to get here.

Sinnoh:
Favorite- They're all kinda meh.
Least Favorite- Maylene. I have no idea why. I just don't care for her.

Unova:
Favorite- Drayden. Badass grandpa.
Least Favorite- Iris. Forever ruined by the anime.

Kalos:
Favorite- Olympia. I love her design.
Least Favorite- Korrina. I just... I don't like her.

Galar:
Favorite- Piers. Babe. Babe. Babe. Babe. Babe.
Least Favorite- Bea (wow we three for three with these female fighting type gym leaders...). Hee hoo fighting type Rei Ayanami. Not know how smile. So serious. Omg she smile! Is big deal!!

Paldea:
Favorite- Larry. My man works hard for the money. So hard for it honey. He needs a vacation. And a new boss.
Least Favorite- Iono. I hate this creature with the passion of 5 million suns. Tell me you don't care about your position as gym leader except to make you hot view money without saying it outright. Why should I humor your stupid influencer gig and miserable personality if I want to become a champion? You won't even battle me if I don't get your ass enough views? Unprofessional. Obnoxious. God I hate this character type.
 
Gen 1
Favorite: Probably Blaine for the implied backstory with Mewtwo's creation. Sabrina is really cool too, but I've seen so many different interpretations of her personality (eerie-but-mostly-nice in the games, borderline possessed by her own powers in the anime, straight-up malicious in Adventures/PokeSpe) that it's hard for me to form a concrete opinion of her.
Least Favorite: Hrrm...Lt. Surge, I guess, for how abrasive he is.

Gen 2
Favorite: Overall Morty--I really like his HGSS design and his interest in Johto lore--but I quite like Jasmine's personality as well. And the fact that she tends a lighthouse; I love lighthouses.
Least Favorite: Clair. Please get over your ego a bit, Clair.

Gen 3
Favorite: I'm kinda neutral on the Hoenn Gym Leaders to be honest. I guess my favorites are Norman for being the only player's dad to appear on-screen and Wattson for his connections to the Sea Mauville/New Mauville conspiracy in ORAS.
Least Favorite: Uhmm...Wallace? I don't even really dislike him. He's a character everyone else (including Game Freak; they made him the Emerald Champion) seems to really like, but I only feel neutral toward, and that just feels a bit awkward.

Gen 4
Favorite: Again, I don't have a strong favorite or least favorite...but I guess my favorite is Roark? I like his design, the fact that you get to meet a family member of his, and his connection to the Underground, one of my favorite things to do while playing Platinum.
Least Favorite: Candice. Again, not a strong dislike...but a miniskirt in a perpetually snowy town doesn't make much sense. PokeSpe even made a joke about it.

Gen 5
Favorite: Brycen, for the weirdly specific reason that he ties together two of my favorite things: Pokémon and the Green Hornet. (Brycen seems to be strongly inspired by Bruce Lee, and one of Bruce Lee's first major roles was Kato in the 1960's Green Hornet TV show). Clay is a close second because I have Texan bias. I know canonically he's actually Sinnohan, but I like to think he or his family made their way to Unova through Orre/unseen other Southwestern-state region, since his outfit really doesn't match what people wear in Unova.
Least Favorite: Skyla. Poketuber and Fakemon artist TrueGreen7 did a video on best character designs for each Gen (in his opinion), and I think he summed up Skyla very well: "Skyla's hot, we all know it, but it's not like this is the most successful interpretation of a Flying-Type trainer. It's an odd design, elevated by how attractive Skyla is." Yes, it is a VERY odd design. They grabbed a normal, kinda-cool jumpsuit and took scissors to it. W H Y. I know why and I know I'm not the target demographic for why, but I hate when designers do this.
Gen 6
Favorite: Clemont. I have a big weakness for gadgeteer characters. I genuinely like Ramos's design as well, but he reeeeaaally didn't get enough screen time.
Least Favorite: Olympia. Not so much a dislike as her vibe just not being my cup of tea.
Gen 7
Favorite: Ryuki by default, since he is the only Gym Leader. :enzap:
Least Favorite: Also Ryuki by default.
Kidding, I'll do Trial Captains for this Gen. (I do find Ryuki really interesting though; I wish we saw more of him.)
Favorite is Acerola for her connections to Alola's lore and history, as well as hosting my favorite Trial in the game. Poor Sophocles and his gadget mishaps, along with his relationship with Molayne, make him my second favorite.
Least Favorite...I've said this a lot, but this is another case where I don't have a super-strong dislike for any of them. I guess Lana? She's not a bad character by any means, but I'm very, very bad at catching on to the tall tales style of pranking she uses, so it makes me a little uncomfortable when people do it to me, in fiction OR real life.
Gen 8
Favorite: Allister. Probably my favorite Gym Leader of all time, honestly. He's kind of a male version of me when I was younger (only having certain people I was comfortable with and barely saying a word outside that circle), so I find him very relatable. He also uses one of my favorite Types and is a lefty!
Least Favorite: This was a really strong batch, but I think I'd have to say Gordie, followed by Melonie. Type preferences is a really silly reason to break up a family. I feel like we should have gotten a little post-game event where we see them start to reconcile, or something. (Melonie gets a bit higher than Gordie since she seems more open to ending the feud.)
Gen 9
Favorite: Brassius. We saw Trainers with whips in Gen 1 (a holdover from a scrapped mechanic where Trainers could fight Pokemon, from what I've heard) and then never saw them again. I thought such things were permanently censored out for being unfitting to the world, but this goofball managed to make it in with a whip. A whip covered in spikes, no less. I'd find him entertaining for that alone, but he also inhabits my favorite Paldean town and is friends with my favorite E4 member and teacher. He ALSO also straight-up explains the meaning of "Surrendering Sunflora" to a classful of kids when it's stated elsewhere that scholars have been debating the meaning of the sculpture for YEARS. That's hilarious and I respect him for it.
Least Favorite: Tulip. Which I feel a little bad for saying, because it's not her fault. I have a completely irrational phobia of makeup for the same reasons she cites it being like "magic": it can completely change your appearance. That's unsettling. It feels like lying, even though I know it's not. Tulip actually triggered a mild fight-or-flight response from me when she threatened offered to give the protagonist a makeover. The heavy eyeshadow isn't a favorite design trait of mine, either, though the art style makes it better (irl, I can't look at someone with heavy eyeshadow in the face very long or my eyes start watering.) I'm sorry you walked into my weird problems, Tulip.
 
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