LiamLols

and the next day she got drunk again and forgot the whole thing

hey guys remember where early seasons Anastasia actually cares about Kevin and even supports him and comfort him?

morning doooodle. made out of pure boredom. I have another version with much more fun colors ..But i dont really like it that much So im gonna keep it to myself

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“Skinner gets called gay”

Skinner gets assumed as a "homersexual" and Homer asks if he's into women - s2 ep14: Principal Charming

Chalmers tells Skinner to be gay on his own time after Skinner says they have horoscopic compatibility - s16 ep17: The Heartbroke Kid

Child draws Skinner kissing a merman as a prank - s17 ep18: The Wettest Stories Ever Told

Skinner is in the middle of explaining how he knows how to slingshot "like all boys" and Nelson cuts him off saying "You like all boys? Hah hah!" - s20 ep11: How The Test Was Won

Skinner AND Chalmers get called the worst-dressed gay men a substitute teacher has ever met - s24 ep15: Black-Eyed, Please

“Wait, IS Skinner gay (bi)?”

Bart tells Skinner to get himself fired from the army by flirting with his commanding officer, which Skinner accepts without hesitation - s5 ep19: Sweet Seymour Skinner's Badaasssss Song

Skinner and Homer are in a hotel for jury duty and Skinner points out that they're like The Odd Couple (with Skinner being like Felix and Homer like Oscar) - s5 ep20: The Boy Who Knew Too Much

Skinner reads a Confirmed Bachelor Magazine while looking over detention - s21 ep4: Treehouse of Horror XX

Skinner kisses Groundskeeper Willie and they both realize they kinda like kissing men and go from uncomfortable to REALLY making out - s21 ep15: Stealing First Base

“Skinner and Chalmers have a... situationship.”

Skinner laughs at an accidental joke Chalmers makes and Chalmers joins him - s4 ep20: Wacking Day

Skinner and Chalmers laugh at the idea of using their oil money to pay the students' scholarships - s6 ep25: Who Shot Mr. Burns? part one

Chalmers teases Skinner and excitedly shows off his new Honda to him - s8 ep7: Lisa's Date With Density

Skinner offers Chalmers to use his Merkur (car) after Chalmers' Camry got destroyed, Chalmers rejects him on the basis that his car is full of Burger King litter - s16 ep5: Fat Man and Little Boy

Chalmers says he wished he and Skinner were closer when Skinner gets killed in front of him - s18 ep4: Treehouse of Horror XVII

Skinner honors the "ding" in "balding" for Chalmers - s18 ep5: G.I. D'oh

Skinner and Chalmers sing a musical number together and Skinner "makes it weird" (according to Chalmers) by complimenting his voice at the end - s18 ep14: Yokel Chords

Chalmers, Skinner and Willie get caught in a Diet Coke and Mentos explosion inside a storage building, Chalmers yells for Skinner but gets no response, gets worried and then when he does respond saying he's alright Chalmers tells him to never scare him like that again - s19 ep13: The Debarted

Chalmers and Skinner create the production company "ChalmSkinn" and do some morally dubious scheming together while wearing atleast 3 matching outfits - s19 ep18: Any Given Sundance

Chalmers tells Skinner they should start eating a cock cannoli that flew in through the window at both ends to hide it from Agnes, and that quote, "They'll know they're safe when their lips meet in the middle", they then proceed without hesitation - s20 ep1: Sex, Pies and Idiot Scrapes

Skinner is confused and upset that Chalmers is "overseeing other principals" and asks what they're going to tell the kids, Chalmers says the kids already know and they're happy for him. This is clearly a breakup allegory. - s20 ep19: Waverly Hills 9-0-2-1-D’oh

Chalmers lays down on Skinner's thigh and tells Skinner to hold his head and say soothing things - s20 ep21: Coming To Homerica

Skinner and Chalmers (and Agnes) have a firework show picnic in the background of a flashback scene - s22 ep10: Moms I'd Like to Forget

Skinner flirts with Chalmers and gets called a regular Casanova by him - s22 ep11: Flaming Moe

Skinner has a dream about being a cowboy and literally rides Chalmers - s25 ep7: Yellow Subterfuge

Demon ChalmSkinn's entire character - s26 ep4: Treehouse of Horror XXV

Skinner and Chalmers rub elbows and laugh about kids not being their problem after 6th grade - s26 ep22: Mathlete's Feat

Chalmers and Skinner share a virtual picnic date together in VR (except Chalmers is dating Skinner's grave in his POV) - s28 ep2: Friends and Family

Kearney asks Skinner if he likes Chalmers so much, why doesn't he marry him? Skinner says that as Superintendent Chalmers is basically married to all of his principals and smiles proudly - s30 ep1: Bart's Not Dead

Skinner performs the heimlich maneuver on Chalmers in a bafflingly suggestive way and uses his shirt and suit jacket as a pillow for him, and then gently strokes his head while saying "You're safe now" - s31 ep1: The Winter of Our Monetized Content

Just. Most of the episode. - s32 ep8: The Road to Cincinnati

Skinner and Chalmers have a Steamed Hams-themed Christmas card decorated with candy canes forming hearts in the credits - s32 ep16: Manger Things

Skinner and Chalmers get inside a closet to privately celebrate having a good, qualified teacher apply to their school - s33 ep18: My Octopus and a Teacher

Just wanted to mention that I watched s20 ep6 - Homer and Lisa Exchange Cross Words (beautiful episode btw almost made me tear up a little) and right at the beginning there's the scene with Edna trying to break up with Skinner (rip) and him misunderstanding it for a proposal.

First of all I thought it was adorable how willing he was to get married, instantly thought to myself 'GARY YOU HAVE TO PUT A RING ON IT NOW!!!!'

Second of all, what really caught my attention is that Homer proceeds to comfort Skinner by saying "What lonely widow wouldn't consider you as an option?" WHAT????? LONELY WIDOW????? LIKE A WIDOWER LIKE GARY CHALMERS?????

I know I'm reaching hard right now and that was just a joke on Skinner's expense as usual, but why that specifically? WHAT were they implying with that.

(also Gary's smile at Skinner in this scene always gets me, it's just so? fond??)

“Skinner gets called gay”

Skinner gets assumed as a "homersexual" and Homer asks if he's into women - s2 ep14: Principal Charming

Chalmers tells Skinner to be gay on his own time after Skinner says they have horoscopic compatibility - s16 ep17: The Heartbroke Kid

Child draws Skinner kissing a merman as a prank - s17 ep18: The Wettest Stories Ever Told

Skinner is in the middle of explaining how he knows how to slingshot "like all boys" and Nelson cuts him off saying "You like all boys? Hah hah!" - s20 ep11: How The Test Was Won

Skinner AND Chalmers get called the worst-dressed gay men a substitute teacher has ever met - s24 ep15: Black-Eyed, Please

“Wait, IS Skinner gay (bi)?”

Bart tells Skinner to get himself fired from the army by flirting with his commanding officer, which Skinner accepts without hesitation - s5 ep19: Sweet Seymour Skinner's Badaasssss Song

Skinner and Homer are in a hotel for jury duty and Skinner points out that they're like The Odd Couple (with Skinner being like Felix and Homer like Oscar) - s5 ep20: The Boy Who Knew Too Much

Skinner reads a Confirmed Bachelor Magazine while looking over detention - s21 ep4: Treehouse of Horror XX

Skinner kisses Groundskeeper Willie and they both realize they kinda like kissing men and go from uncomfortable to REALLY making out - s21 ep15: Stealing First Base

“Skinner and Chalmers have a... situationship.”

Skinner laughs at an accidental joke Chalmers makes and Chalmers joins him - s4 ep20: Wacking Day

Skinner and Chalmers laugh at the idea of using their oil money to pay the students' scholarships - s6 ep25: Who Shot Mr. Burns? part one

Chalmers teases Skinner and excitedly shows off his new Honda to him - s8 ep7: Lisa's Date With Density

Skinner offers Chalmers to use his Merkur (car) after Chalmers' Camry got destroyed, Chalmers rejects him on the basis that his car is full of Burger King litter - s16 ep5: Fat Man and Little Boy

Chalmers says he wished he and Skinner were closer when Skinner gets killed in front of him - s18 ep4: Treehouse of Horror XVII

Skinner honors the "ding" in "balding" for Chalmers - s18 ep5: G.I. D'oh

Skinner and Chalmers sing a musical number together and Skinner "makes it weird" (according to Chalmers) by complimenting his voice at the end - s18 ep14: Yokel Chords

Chalmers, Skinner and Willie get caught in a Diet Coke and Mentos explosion inside a storage building, Chalmers yells for Skinner but gets no response, gets worried and then when he does respond saying he's alright Chalmers tells him to never scare him like that again - s19 ep13: The Debarted

Chalmers and Skinner create the production company "ChalmSkinn" and do some morally dubious scheming together while wearing atleast 3 matching outfits - s19 ep18: Any Given Sundance

Chalmers tells Skinner they should start eating a cock cannoli that flew in through the window at both ends to hide it from Agnes, and that quote, "They'll know they're safe when their lips meet in the middle", they then proceed without hesitation - s20 ep1: Sex, Pies and Idiot Scrapes

Skinner is confused and upset that Chalmers is "overseeing other principals" and asks what they're going to tell the kids, Chalmers says the kids already know and they're happy for him. This is clearly a breakup allegory. - s20 ep19: Waverly Hills 9-0-2-1-D’oh

Chalmers lays down on Skinner's thigh and tells Skinner to hold his head and say soothing things - s20 ep21: Coming To Homerica

Skinner and Chalmers (and Agnes) have a firework show picnic in the background of a flashback scene - s22 ep10: Moms I'd Like to Forget

Skinner flirts with Chalmers and gets called a regular Casanova by him - s22 ep11: Flaming Moe

Skinner has a dream about being a cowboy and literally rides Chalmers - s25 ep7: Yellow Subterfuge

Demon ChalmSkinn's entire character - s26 ep4: Treehouse of Horror XXV

Skinner and Chalmers rub elbows and laugh about kids not being their problem after 6th grade - s26 ep22: Mathlete's Feat

Chalmers and Skinner share a virtual picnic date together in VR (except Chalmers is dating Skinner's grave in his POV) - s28 ep2: Friends and Family

Kearney asks Skinner if he likes Chalmers so much, why doesn't he marry him? Skinner says that as Superintendent Chalmers is basically married to all of his principals and smiles proudly - s30 ep1: Bart's Not Dead

Skinner performs the heimlich maneuver on Chalmers in a bafflingly suggestive way and uses his shirt and suit jacket as a pillow for him, and then gently strokes his head while saying "You're safe now" - s31 ep1: The Winter of Our Monetized Content

Just. Most of the episode. - s32 ep8: The Road to Cincinnati

Skinner and Chalmers have a Steamed Hams-themed Christmas card decorated with candy canes forming hearts in the credits - s32 ep16: Manger Things

Skinner and Chalmers get inside a closet to privately celebrate having a good, qualified teacher apply to their school - s33 ep18: My Octopus and a Teacher

I've also found this other commentary with some more simpsons writers, and there's this one part they mention how they, and quote, "love the SkinnerChalmers dynamic, these two together are magical" and I just think that's neat