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* In one episode of ''Series/TheJeffersons'', George meets up with his old Navy friend Eddie and finds that she is now Edie. For 1997, this was a surprisingly sensitive early use of a trans character (and a black one at that). Of course, it has the George-freaks-out-initially-but-learns-to-accept-it storyline.
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* In one episode of ''Series/TheJeffersons'', George meets up with his old Navy friend Eddie and finds that she is now Edie. For 1997, 1977, this was a surprisingly sensitive early use of a trans character (and a black one at that). Of course, it has the George-freaks-out-initially-but-learns-to-accept-it storyline.
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* One of the protagonists of ''VideoGame/XenobladeChronicles3FutureRedeemed'' is A, whose true identity is [[spoiler:the masculine-presenting Alvis from the [[VideoGame/XenobladeChronicles1 first game]], who now has a feminine-looking body and identifies with no set of pronouns at all]]. The first thing Shulk tells to A when they talk one-on-one is that he recognizes A as the same old friend he's always known where it matters, and while he is initially confused by A's different appearance, he is completely understanding once Rex explains that Ontos is in-between male and female.
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* The ''Website/{{Pixiv}}'' one-shot comic ''Childhood Friend Yuri'' tells a story about a pair of childhood friends who implied to be separated during childhood and reunite by chance at college. At first, the protagonist is shocked after her childhood friend comes out as trans woman, but she quickly learns about her gender identity and accepts her for who she is.
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* ''Webcomic/ChildhoodFriendYuri'' During their eventual reunion at college, The ''Website/{{Pixiv}}'' one-shot comic ''Childhood Friend Yuri'' tells a story about a pair of childhood friends who implied to be separated during childhood and reunite by chance at college. At first, the protagonist is Protagonist initially shocked after that a girl who greets her is turns out to be her childhood friend comes out as trans woman, but friend, that she quickly learns about her gender identity and accepts her for who remembers as a guy. The Childhood Friend then explains casually that she is.hasn't done bottom surgery yet.
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* 'I Guess My Childhood Friend Wasn’t a Boy.'' which as the title suggests, tells a story of a pair of childhood friends who reunited during adulthood and how the protagonist find out that her childhood friend is a trans woman.
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* In ''Series/TwoAndAHalfMen'', notorious womanizer Charlie is invited to a bar to meet up with an old girlfriend to talk. He meets an attractive man there (played by Chris O'Donnell), whom he befriends, only to discover he is Charlie's ex-girlfriend, who came out as transgender after they broke up. This culminates in Charlie's mother Evelyn (briefly) dating this man.
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* In ''Series/TwoAndAHalfMen'', notorious womanizer Charlie is invited to a bar to meet up with an old girlfriend named Jill, only to talk. He meets an attractive find that his ex has transitioned and is now a handsome man there named Bill (played by Chris O'Donnell), whom O'Donnell). Although they become friends again, Charlie is quietly disturbed by the idea that he befriends, only to discover he is slept with a man and starts wondering if he's gay. Then Bill starts dating Charlie's ex-girlfriend, who came out as transgender after they broke up. This culminates in Charlie's mother Evelyn (briefly) dating mother.
-->'''Alan:''' Do you realise what thisman.means?
-->'''Charlie:''' Yes! I slept with a woman who wanted to be a man! Or... I slept with a man in a woman's body! Or -- and this is my new favorite, and the title of my autobiography -- my mom and I slept with the same dude!
-->'''Alan:''' Do you realise what this
-->'''Charlie:''' Yes! I slept with a woman who wanted to be a man! Or... I slept with a man in a woman's body! Or -- and this is my new favorite, and the title of my autobiography -- my mom and I slept with the same dude!
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* In ''VideoGame/{{Catherine}}'', the waitress of the bar that Vincent and his friends hang out in is named Erica. They speak closely with her and banter as if they've known her for a long time and Tobey, the only one in the group who's not a thirty-something, develops a bit of a crush on her. One night he happily tells Orlando that he lost his virginity to Erica, but there was something about her that he couldn't quite put his finger on. In the best ending of Katherine's path, while everyone is at the bar for Vincent and Katherine's wedding reception, Tobey exasperatedly tells the gang that they didn't tell him that Erica is transgender; they reveal that they all went to high school together and she used to go by "Eric"; she underwent gender reassignment surgery and they've been referring to her with her name and she/her pronouns since. She simply tells him that there are no refunds on his V-card.
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* In ''VideoGame/{{Catherine}}'', the waitress of the bar that Vincent and his friends hang out in is named Erica. They speak closely with her and banter as if they've known her for a long time and Tobey, the only one in the group who's not a thirty-something, develops a bit of a crush on her. One night he happily tells Orlando that he lost his virginity to Erica, but there was something about her that he couldn't quite put his finger on. In the best ending of Katherine's path, while everyone is at the bar for Vincent and Katherine's wedding reception, Tobey exasperatedly tells the gang that they didn't tell him that Erica is transgender; they transgender. They reveal that they all went to high school together and she used to go by "Eric"; she underwent gender reassignment surgery and they've been referring to her with her name and she/her pronouns since. She simply tells him that there are no refunds on his V-card.
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* In ''VideoGame/{{Catherine}}'', the waitress of the bar that Vincent and his friends hang out in is named Erica. They speak closely with her and banter as if they've known her for a long time and Tobey, the only one in the group who's not a thirty-something, develops a bit of a crush on her. One night he happily tells Orlando that he lost his virginity to Erica, but there was something about her that he couldn't quite put his finger on. In the best ending of Katherine's path, while everyone is at the bar for Vincent and Katherine's wedding reception, Tobey exasperatedly tells the gang that they didn't tell him that Erica is transgender; they tell him that they all went to high school together and she used to go by "Eric"; she underwent gender reassignment surgery and they've been referring to her with her name and she/her pronouns since. She simply tells him that there are no refunds on his V-card.
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* In ''VideoGame/{{Catherine}}'', the waitress of the bar that Vincent and his friends hang out in is named Erica. They speak closely with her and banter as if they've known her for a long time and Tobey, the only one in the group who's not a thirty-something, develops a bit of a crush on her. One night he happily tells Orlando that he lost his virginity to Erica, but there was something about her that he couldn't quite put his finger on. In the best ending of Katherine's path, while everyone is at the bar for Vincent and Katherine's wedding reception, Tobey exasperatedly tells the gang that they didn't tell him that Erica is transgender; they tell him reveal that they all went to high school together and she used to go by "Eric"; she underwent gender reassignment surgery and they've been referring to her with her name and she/her pronouns since. She simply tells him that there are no refunds on his V-card.
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* DiscussedTrope in ''Fanfic/ThePowerOfFriendshipAndThisGunIFound'' between Seto and Mai on their way to break into Pegasus' mansion. Pegasus was a cross between a CoolUncle and a ParentalSubstitute to Mai when she was pre-transition, but in the seven years since they've last seen each other she has undergone Gender Affirmation surgery and been on hormones for years.
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* ''Series/DoctorWho'': At the end of "[[Recap/DoctorWhoS34E11DarkWater Dark Water]]", it is [[TheReveal revealed]] that the Doctor's old FriendlyEnemy the Master has become the ''Mistress'', and now goes by Missy. For years, there had been fan speculation that Time Lords can change sex when they [[ResurrectiveImmortality regenerate]], and this was the first onscreen example. The Doctor is shocked that the Master is alive, not that the Master is female.
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* ''Series/DoctorWho'': At the end of "[[Recap/DoctorWhoS34E11DarkWater Dark Water]]", it is [[TheReveal revealed]] that the Doctor's old FriendlyEnemy the Master has become the ''Mistress'', and now goes by Missy. For years, there had been fan speculation that Time Lords can change sex when they [[ResurrectiveImmortality regenerate]], which was confirmed by statements the Doctor made about the Corsair in [[Recap/DoctorWhoS32E4TheDoctorsWife "The Doctor's Wife"]], and this was the first onscreen example. The Doctor is shocked that the Master is alive, not that the Master is female.
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* ''Webcomic/ElGoonishShive'': The Sister arc has this when Elliot is turned into a girl (specifically a supernaturally attractive girl). He can't actually tell any of his classmates, instead claiming to be "Elliot's cousin Ellen," which results in at least one example of Tony flirting with him while also trash-talking him. Elliot, of course, proceeds to hit Tony with a giant hammer in response.
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* A variant in ''VideoGame/BaldursGateIII''. Shadowheart supported her friend Nocturne's transition years ago and has been at her side ever since. Except before the start of the game, almost all of Shadowheart's memories were erased for a mission. She can remember a child Nocturne before her transition if she eats the Noblestalk mushroom; when Shadowheart visits the House of Grief in the third act, from her perspective, she meets a distant childhood friend who is now female.
