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Webcomic / Thinking Too Much to Think Positively

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Xan's definitely overthinking something with that look on her face.

Thinking Too Much to Think Positively is a humourous autobiographical webcomic by Xanthippe "Xan" Hutcheon (who would later go on to do Pandora's Tale). A mixture of Slice of Life and Gag Series, it chronicles the goings-on in its author's life as a trans woman in the 21st century with a heavy dose of humour. Xan's friends occasionally feature in the comic as side characters. Though the mood is usually funny, the strip can be downbeat at times.

You might know this comic best from when Xan did a visual guide to various pride flags that went viral in 2018note .

Read the comic here.

This comic contains examples of:

  • A-Cup Angst: Discussed by Xan in a few comics, as she's not happy with the lack of progress her chest has made on HRT. In "Xanatomy", she labels her breasts with "Work in progress, please check back later".
  • Added Alliterative Appeal: A rather sombre example in the "Dial D for Dysphoria" four-parter, where all of the words Xan uses to describe the feelings gender dysphoria gave her all begin with the letter D. Examples include "dissociation", "disgust", "distress" and "disgraceful". However it ends on a happy note where the last word is "discovery".
  • Already the Case: In "Bathroom Anxiety", the Cis Fairy tries taunting Xan about being scared to use the women's restroom, pointing out several ways she desperately avoids the possibility of interacting with or having to acknowledge anyone else while in there. However, the taunt falls flat because that's exactly how Xan was already acting when using the men's restroom before.
  • Amazing Technicolor Population: A very downplayed example applying only to one character - Xan herself. She deliberately draws herself with literal white skin - while all other white humans have realistic flesh tones - to represent how she sees herself as a work in progress. To add to this, in the first part of "Dial D for Dysphoria", the colour literally disappears from Xan when she experiences gender dysphoria for the first time.
  • Bespectacled Cutie: In "Looking Good", after getting glasses for the first time, Xan figures she probably won't wear them often... until she gets some compliments on the cute aesthetic, at which point she decides she's never going to take them off.
  • Breast Attack: In "Sense and Sensitivity", Xan manages to accidentally punch herself in the boob, which hurts enough to make her cry. The Rant gripes that this managed to happen when they're not even that big of a target.
  • Cathartic Crying: Happens to Xan in "Happy With Sadness" after years of more-or-less repressing her emotions due to growing up feeling disconnected from herself.
  • Couch Gag: The colours in the comic's logo change in each strip, as well as the portrait of Xan next to it.
  • Cruel to Be Kind: Discussed in "A Boy Named Sue 2: Electric Suegaloo"; as in the original song, Sue's dad named him that expecting him to be mocked for his Gender-Blender Name, which in turn would make him toughen up. However, people were actually very understanding, and Sue has instead become a kind and thoughtful man proud of his name, and was only seeking his father out to learn the reason for his unusual name. When he learns the truth, he's disappointed.
  • Drugs Are Bad: Parodied in "This is Your Brain on Estradiol"; a woman named Beatrice does an anti-drug PSA, attempting to cite her history with drugs in an attempt to Scare 'Em Straight, but she actually hasn't experienced any negative consequences at all, and she's forced to awkwardly guess that she might have "used up all the good luck" about it before the whole thing is shut down.
  • Early-Installment Weirdness: In early comics Xan was non-binary rather than a trans woman as she wasn't quite sure whether she was female yet.
  • Easy Sex Change: In "Sexchange Student" Xan recounts how stories of gender affirming surgery she heard as a child were exaggerated in this fashion. Child Xan imagines a magical procedure called a "sex change operation" that apparently transforms men into women overnight.
  • Fake Memories: Discussed in "Death of a Memory". Xan recounts how she thought a video game magazine she read as a child had an ad for Sailor Moon VHS tapes, only to discover the issue in question never had such an ad.
    Xan: I think, over time, my memory fused elements of both VHS covers togethernote , and the name Sailor Moon became associated with them both. As I saw snippets of Sailor Moon over the years, these filled in the gaps, creating this new memory from fragments of others.
  • Feghoot: In "Pride Crossover", Pandora appears in several pride-flag-themed outfits with her name changed accordingly ("Bidora", etc)... until the asexual Pandora, "Adora", is instead an asexual-themed Adora.
  • Good Angel, Bad Angel: Early on as Xan was figuring out her gender identity, she would be sometimes be visited by two characters similar to this trope called the Cis Fairy - who tried to convince Xan she was really a confused cis man - and the Trans Fairy, who would tell Xan to accept the fact she's trans. Here's an appearance from them.
  • Hate Sink: The blond-haired man who occasionally shows up to act condescending towards Xan.
  • Have I Mentioned I Am Heterosexual Today?: Xan's past self is guilty of denying she was a closeted trans woman. Examples from "Lies I Told Myself":
    I only play as girl characters because they look cooler.
    My discomfort with masculinity is just because I'm a feminist.
    Cosplaying exclusively as female characters is just a bit of fun. Everyone does it!
  • Hide Your Lesbians: Discussed in "Lesbian Lizards" when Xan mentions how the female-only Pokémon Salazzle is based on the New Mexico whiptail, an exclusively female species of lizard that reproduces asexually:
    Xan: However it seems that a lesbian Pokémon was deemed insufficiently family-friendly, and so they made it a dominatrix instead.
  • Idiosyncratic Episode Naming: Nearly every comic title is a pun.
  • Innocent Innuendo: In "Car Trouble Entendre", Xan notes that American car repair places tend to have oddly homoerotic names, citing "Pep Boys" and "Jiffy Lube". Then a sign for "Crankshaft Grinders" comes up.
  • Lazy Artist: In "It's a Commitment", while getting a tattoo, Xan realizes to her dismay that she'll have to draw that tattoo on her Author Avatar from now on. RF snarks that this clearly doesn't follow, since she already doesn't draw RF's tattoos.
  • LGBT Awakening: In "Moment of Impact", a random cis boy is helping Disgruntled Catgirl out with Pride, and she recalls that she was a "passionate ally" much like him before she knew she was trans, as a way of working with her feelings without addressing them. The "boy" suddenly sprouts cat ears as "he" puts the pieces together.
  • Long Hair Is Feminine: A downplayed/subverted example with the closeted Xan as she wears her hair down to her chin, though not as long as she would after transitioning, where it now touches her shoulders.
  • Medium-Shift Gag: In "High Definition World, Xan mentions that her vision is a little blurry and tries on a friend's new glasses. The next panel is a photograph. The Rant below the comic jokes that Xan had previously considered the comic's simplified cartoony style to be "realistic".
  • My Future Self and Me: In "Future Tense", child Xan meets up with present-day Xan after summoning the latter via a coin-operated machine. At first it goes awkwardly, but once the Elephant in the Living Room of Xan transitioning is dealt with, child Xan asks her adult self what the future is like:
    Present!Xan: Well... Claire's Accessories is just called Claire's now...
  • No Name Given: The spiky blond-haired man (see Hate Sink above) hasn't been named in the comic yet.
  • Pink Girl, Blue Boy: In the "displaced" part of "Dial D for Dysphoria", the boys are grouped into a blue background, the girls into pink and the confused, dysphoric teenage Xan into Gloomy Gray.
  • Pungeon Master: Xan is very fond of puns. You'd be hard-pressed to find an installment where she doesn't make a pun.
  • A Real Man Is a Killer: "A Boy Named Sue" reinterprets the Shel Silverstein song by that namenote , showing that Sue's dad is positively delighted that he's become "a rage-filled shell of a man" rather than "some pansy doctor or lawyer". Sue isn't happy.
  • Queer Colors: Xan compares some Pokémon to pride flags based on their respective colour schemes in "Pokémon That Look Like Pride Flags".
    RF (Xan's partner): It's weird that there isn't a Pokémon for the rainbow flag.
    Xan: Well, technically Ho-Oh is the Rainbow Pokémon.
    [Ho-Oh is shown in front of a rainbow flag, the two clearly don't match well.]
    RF: That's not a rainbow! That's two-thirds of a rainbow at best!
    Xan: In the Gameboy era, that was more colours than our brains could handle!
  • Queer Establishing Moment: Xan being referred to as female by her partner, RF, in "They Said, She Said" helps her come to terms with being a trans woman. At the time of publication she was non-binary but beginning to get more accustomed to being referred to as female. Xan being a trans woman then sticks for the rest of the comic.
    RF: Hey everyone, this is my girlfriend Xan! Isn't she cute?
    [Xan blushes sweetly and literally glows with the trans pride colours.]
    RF: Yeah, I think you're good.
  • Separated by a Common Language: In "British Trans Humour", the British-born Xan jokes post-orchiectomynote  that she's "two stones lighter". Her friends who are familiar with British English find it funny, the nameless blond man doesn't get it.
  • Trans Chaser: In "Mystery Men", Xan describes the phenomenon of her and other trans women being followed by creepy men on Twitter whose likes are full of trans pornography. She discusses the possibility that these men consider being trans a fetish, and they hope that the women they follow will admit they have a fetish and start posting trans porn themselves.
  • Trans Tribulations: Many comics show that life as a trans woman is not easy for Xan.
    • In "Camera Shy", Xan worries that she won't look feminine enough when a film crew comes to her workplace.
    • In "Self, Self, Self", Xan realises how much she relies on validation from strangers due her poor self-image and that due to having to wear a face mask during the pandemic, she'll be misgendered a lot more.
    • There's a four-part story called "Dial D for Dysphoria" (parts 1 and 2, parts 3 and 4) where Xan recounts the various negative feelings she's had about being unable to understand gender dysphoria over the years.
    • Played for Black Comedy in the appropriately-titled "Tragicomedy"; when the annoying blond guy gripes about Obnoxious In-Laws, NewGenderWhoDisnote  jokes that he should date a trans person — since trans people are often rejected by their families, there will be no in-laws to worry about. The blonde guy is appalled.
  • Twofer Token Minority: A rare threefer examle - Xan describes herself as a "fat, blue-haired transsexual" in "Some Kind of ID" in regards to her workplace introducing photos to the ID cards:
    Xan: But who's not gonna recognise me? I'm the fat, blue-haired transsexual who's worked there for years! I am literally the most distinctive person there and I shouldn't need to wear a photo ID to prove who I am.
  • Your Other Left: In "Cycle Analysis", Xan notes that when a cyclist calls "on your left" to warn that they're going to be passing her on the left, her first instinct is to hear "left" and move herself to the left.