Old Friend, New Gender

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Kor: Curzon, my beloved old friend!
Jadzia: [laughing] It's Jadzia now.
Kor: Jadzia, my beloved old friend!

— Star Trek: Deep Space Nine, "Blood Oath"

At a Class Reunion or other gathering of long-parted friends and acquaintances, a male regular character meets (and, in some cases, hits on) a stunningly beautiful woman. While he is certain he's never met her before, she is distressingly familiar with all manner of details about his life, and seems privately amused by the whole encounter.

Eventually the truth comes out: she is in fact a former male classmate (sometimes even a former best friend) who has undergone gender reassignment and come out of it a bombshell. While beautiful trans women are not uncommon in Real Life, the prevalence of supermodels and Playboy Playmates in these parts usually means we're more in the realm of the Easy Sex Change.

In most cases, the regular cast member freaks out, entertaining the audience with his inability to cope with either the concept, the execution, or his attraction to the woman. In those cases where he accepts his friend with aplomb, there is usually An Aesop blatantly made about tolerance and the like.

At times, this trope involves a male character's ex-"girlfriend" undergoing female-to-male gender reassignment and meeting the now male character, who goes unrecognized. These examples will sometimes have the regular cast member consider outing the trans character as such when he sees him hitting on a female character.

See also Unsettling Gender-Reveal.

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Examples:

Advertising

• Holiday Inn ran a memorable commercial based on this trope during Super Bowl XXX. It was pulled after just one airing due to complaints from both a Media Watchdog and gay-rights group.
• An advertisement for Heinz Baked Beans used this trope. Two men who kissed during summer camp once years ago meet and the cis man is visibly unnerved.
• There exists a Spanish-language ad for Sprite where a group of friends from school reunite as adults and joyfully call out their old nicknames (which thanks to growing up are now Ironic Nicknames) and hug. At the end they're approached by a woman, who they recognize as "Oso" (bear) and embrace.

Anime & Manga

• One chapter of Ai no Shintairiku has Sara go to a class reunion where a bunch of people she knew in elementary are. They don't know who she is at first, but when she reveals the truth to them, they start ambushing her with questions and making her uncomfortable.
• Ayakashi Triangle: After Matsuri is made female, he starts living as a girl to maintain The Masquerade, and ends up talking to Suzu's family for the first time in years. They're practically the only Muggles who knew him when he was male, and so assume a non-transgender variant of this trope: that Matsuri was always a (cisgender) girl they just mistook as male until "she" hit puberty.
• Akane from Bokura no Hentai had known about Marika's desire to live as a girl for years, but it still surprises her when Marika starts living as a girl after being gone from school for several weeks. She continues to call her "Yuuta", though it's not meant to be malicious but due to habit.
• In A Choice of Boyfriend and Girlfriend, middle school Childhood Friends Kazuma and Haruka reunite in Tokyo after 7 years apart as part of a promise they made. Their reunion is played for equal parts laughs and heartwarming, when Kazuma admits to a girl he meets at a local train station how highly he thinks of Haruka, unaware that she was actually Haruka himself — having contracted a condition that irreversibly turned him female and kept the act up until the last possible minute before he accidentally outs himself. The series focuses on Haruka's attempts to settle into the big city, while Kazuma adjusts to how his best friend lives life as a girl.
• The Unsettling Gender-Reveal aspect is inverted in The Day of Revolution: Megumi's former True Companions don't start hitting on her until after they've forced her to confess she used to be their (male) friend Kei.
• Played for Drama in Family Compo: one of Yukari's female classmates used to have feelings for her when Yukari lived as a man, and now that said classmate's marriage is in ruin, she laments how she didn't pick Yukari for husband back then. On the other hand, now that Yukari is a woman, she understands her plight as a fellow lady.
• This is the plot of Go Go Ichigo. An elementary school girl is surprised when the new girl turns out to have been her Forgotten Childhood Friend from kindergarten. Anzu spends most of the manga in confusion and denial, especially due to her falling for Ichigo, and constantly tries to "expose" her to others but eventually she considers Ichigo a girl.
• Averted by Mamiya and subverted by Sagara of Kanojo ni Naru Hi (The Day He Becomes a Girl) and its sequel Kanojo Ni Naru Hi Another. Both change sexes due to a natural process that maintains a fixed gender ratio, so it doesn't particularly surprise anyone. Mamiya does gradually develop a romantic relationship with her best friend after she transitions but that falls under Jumping the Gender Barrier. Sagara is a subversion because he did not accept gender reassignment to go along with the physical sex change. His relationship with a male classmate falls under If It's You, It's Okay. Played straight with Kurokawa: Sagara is very surprised to discover she was a boy he knew (admittedly not well) in grade school.
• This happens at the beginning of Kyou Kara Yonshimai, but with family instead. After being away at college for two years, three girls find out their brother is returning only to find he's living as a woman. After being varying degrees of upset for a while they get over it.
• In Moriarty the Patriot, when James Bond (formerly Irene Adler) meets up with Hudson and John again after his transition, they carefully refer to him by his new name and Sherlock says his appearance might be different, but he's still the same person.
• Happens early in Moyashimon. Kei is introduced as a male college student going to the same school as his childhood friend, disappears for several chapters, and reappears wearing an Elegant Gothic Lolita getup. Sawaki didn't notice that the goth girl was Kei until he noticed that they shared the same microbe and Kei kissed Sawaki.
• The premise of No Bra is that two childhood friends meet, with one now living as a girl. This is later subverted, as the childhood friend was someone else, a tomboyish girl of the same name.
• Played with in Wandering Son. Shiina and Yuki weren't friends as children, but they knew each other. Sometime before the manga began, they met again and eventually paired up. Late into the series, there is a class reunion, but Yuki refuses to go, averting this situation.
• One episode of You're Under Arrest! has an old friend of Aoi asking for help as her younger brother is being bullied. She knows that Aoi works at the police department, but Aoi ends up hiding from her and later on presents as a different individual. The woman learns for herself who Aoi is when she notices her basketball skills (golf in the manga).
• A tragic version appears in Yuureitou. Tetsuo was engaged to a man by his adopted mother when he lived as a woman. He eventually told his fiance he could not marry him, for he did not like men and he identified as male, but hoped they could be like brothers. His fiance was considerably confused, and not soon afterwards, Tetsuo killed his adopted mother and "died". When they meet again, Tetsuo's fiance is horribly disfigured and does not know this. He doesn't know anything about Tetsuo transitioning or the incidents in the past. He still sees Tetsuo as a woman and Tetsuo keeps up the facade of romance until his fiance dies protecting him.

Comic Books

• In Walter Moers' Adolf the Nazi Pig, Adolf Hitler, having emerged from the sewers of Berlin in The '90s, gets a prescription for a fuck from his psychiatrist. The only hooker willing to do prescription sex is Hermine — who turns out to be Hermann Göring after a CIA-sponsored gender change. They do it anyway, singing the "Ride of the Valkyries" in the course — Göring because he still kind of has the hots for Hitler, and Hitler because he is high on crack.
• The Boys: In the epilogue Dear Becky, Wee Hughie's friend Bobby (who was shown to be a Crossdresser in the miniseries Highland Laddie) now identifies as transgender and goes by Bobbi.
• Inverted in one Doctor Fate comic when a character takes most of a page to notice that the previously male Doctor Fate is a woman. (Since this version of Doctor Fate is a man and woman fused into one, and the character in question is the human incarnation of a godlike Lord of Order, this actually makes some sense, but is still played for laughs.)
• Downplayed with one of Hob Gadling's relationships over his muti-century life in The Sandman (1989), as the "boy" was a girl pulling a Sweet Polly Oliver, but Hob met a girl named Peg would was posing as a cabin boy named "Jim" (who was aware she was getting too old to keep it up much longer) in the 1910s. Hob would later say he married a woman named Peg, and Neil Gaiman confirmed that it was Peg/"Jim", which means they got together after Peg got too old to pose as a boy.

Fan Fiction

• In chapter 13 of Denounce the Evils, after several years, Team Rocket comes across Harley, who is now living as a woman. They take to the pronoun change instantly.
• A Fairytale is a Metaphor is a non-fantasy AU of Ever After High featuring Raven as a trans girl. After her mother's death, Raven moves back to her hometown of Everest. The conservative Apple doesn't know how to react to her Childhood Friend's transition.
• New Century 2318, a Neon Genesis Evangelion far-future AU, pulls a particularly spectacular version of this trope on Gendo Ikari.
  Gendo: You're not my son.
  Natsu (formerly Shinji): Was it the way I fill out this dress that gave it away?
• Discussed Trope in The Power of Friendship (And This Gun I Found!) between Seto and Mai on their way to break into Pegasus' mansion. Pegasus was a cross between a Cool Uncle and a Parental Substitute 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.
• RWBY: Scars: When Ruby's aunt Ivory sees her for the first time since Ruby was an infant, she's initially confused because Summer had a son named Crimson. She asks Ruby if she has an older brother, which Ruby declines, but it's obvious to Ivory that Ruby is her niece's kid. Ivory loves Ruby just the same nevertheless.
• In the first chapter of You Got HaruhiRolled!, Kyon meets an attractive girl. She turns out to be Koizumi, frequent source of Ho Yay in the source material.

Film — Live-Action

• In Escape from L.A., Snake Plissken is astonished to discover his old friend Carjack Malone is now Hershe Las Palmas (played by Pam Grier).
• This is the twist ending of the 2019 French film La Grande Classe; the woman who has been talking to and advising one of the protagonists at his middle-school reunion — and who ends up getting together with him — turns out to have been one of his former (male) bullies.
• One classic Filipino film, Miguel/Michelle, has this as the plot with a respectable 'man' returning from being a contract worker as a woman. The situation was not played for laughs, highlighting the social tension transgender people usually experience.
• The slide show in National Lampoon's Class Reunion reveals that a person from their class who'd never taken gym is now a housewife in another state. Whether or not the character is transgender (they may instead have been cross-dressing in their youth) is left unspecified.

Literature

• In Pedro Almodóvar's novel Pornstar, there's a FAAB variant. The titular female pornstar's childhood friend, who had a hopeless crush on her, became a man to be with her (but it didn't work out).
• In Rick, the title character reunites with Melissa, the protagonist of the previous book. He knew her as George when they were in First Grade, but Melissa quickly corrects him that she doesn't use that name anymore.
• The Vorkosigan Saga novel A Civil Campaign features an inversion of the usual examples, with Ivan Vorpatril arriving at the shuttleport with flowers in hand hoping to restart his old relationship with Lady Donna Vorrutyer. He knew she went to Beta Colony concerning something involving the Succession Crisis surrounding her late brother Count Vorrutyer, but it took several seconds for him to realize who that fellow accompanying the two Vorrutyer armsmen was.

Live-Action TV

• An old friend of Dr. John Becker is a trans woman in an episode of Becker ("He Said, She Said"). Despite jokes earlier in the episode completely contradicting this reveal.
• A skit from a different Israeli skit show, The Chamber Quintet, showed a man meeting his old friend from the army, only to discover she's transitioned. He’s extra-shocked by the change because at one point, when it was extra-cold out in the field, they had to share a night of particular closeness... which, at the end of the skit, they choose to re-live.
• Billy Kronk on Chicago Hope ends up meeting a woman who claims to be the sister of a guy who played hockey with him many years before. They end up sleeping together. He starts to suspect that she has fake boobs. When confronting her, she admits that she's not the guy's sister... she is the guy.
• In The City (1995), gorgeous model Azure C. confessed to her landlord Bernardo that she'd had a crush on him since high school. This confused him, as he didn't remember her. Shortly after they consummated their relationship, he learned that she was Transgender. It was the pre-transition version of her who'd had who'd had the crush on him, developed after he protected her from bullies.
• Community references this trope in "Anthropology 101" with Abed asking if Jeff had, "A wealthy uncle, or buddy that may have had a sex change?" and Jeff realising that Abed is mining his life for classic sitcom plots.
• Dead of Summer: It turns out that Blair and Drew were friends at camp before when they both had attended. However, as Drew was then still presenting as a girl with his deadname Andrea as his mom then insisted, Blair didn't recognize him later after they met again and began a romance. Drew, a trans boy, was by then presenting himself as male, which included his name being changed.
• Doctor Who: At the end of "Dark Water", it is revealed that the Doctor's old Friendly Enemy 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 regenerate, which was confirmed by statements the Doctor made about the Corsair in "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.
• In a twist, one of the main characters of The Education of Max Bickford, a professor at the same college Max teaches at, undergoes gender reassignment surgeries just as the series starts.
• Frasier: Parodied when an old friend of Martin's thinks Roz is Niles after surgery.
• In the French-Canadian series Un gars, une fille (Love Bites for the American adaptation), Guy and Sylvie, the show's focus couple are participating in the gay pride parade to support Guy's lesbian sister. There, Guy meets a hot woman named Martine (of whom Sylvie is uncharacteristically not jealous), who claims they went to high school together, and even slept in the same bed during a hockey tournament. Guy is completely confused until Martine reveals she used to be called Martin. When she leaves, Guy, dumbfounded, tells Sylvie he slept with her in high school, not entirely realizing what it implies. Off Sylvie's confused look.
• In one episode of The Jeffersons, George meets up with his old Navy friend Eddie and finds that she is now Edie. For 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.
• Judging Amy: In the "Slade's Chophouse" episode, Bruce looks forward to a visit from his old friend, Father Ted. Bruce is rather surprised that he goes by Teresa now and is in town for the final surgery.
  Amy: Thought you'd be shorter... and a guy.
• An old friend of Finch's (played by Jenny McCarthy) turns out to be a trans woman on Just Shoot Me!. Finch has a difficult time dealing with his attraction to her.
• One skit from the Israeli show Ktzarim shows a class reunion in which every member used to have a nickname related to what they were known for, and which has become irrelevant: a classmate known for playing the guitar lost an arm, another who was known for his hair went bald, etc. The well-endowed one... doesn't have the equipment anymore.
• Played straight on Las Vegas, with a much faster cooldown than usual: Danny McCoy walks into a traffic control, starts hitting on the hot woman to get info, and she asks him if he recognizes her before revealing she's an old friend. Danny is already tolerant, just a little shocked. The next scene has her going out to eat hot dogs while chatting with Danny.
• Used in an episode of Legit (2013) when Steve finds out at a high school reunion that Mary Fulcher, the girl he lost his virginity to, is now Mark Fulcher. He's a little freaked out at first, but he gets over it before long (with the help of some liquor).
  Steve: I am proud that I hit that!
• The Lone Gunmen: Byers's former college friend asks the team for help. About three quarters of the way through, her brother uses her deadname and former pronouns, revealing to the rest of the team that she is transgender. Byers knew her pre-transition (and Jimmy had figured it out) but didn't think it was relevant enough to reveal to the rest of the team.
• Kristy McNichol played Gopher's former college roommate on an episode of The Love Boat.
• In the Married... with Children episode "Dud Bowl", Al gathers his old high school friends for a football game, and it turns out one of them transitioned in the interim. Unlike most examples, this one is played by a male actor (Drew Pillsbury) in drag.
• In Necessary Roughness, Jeanette goes to her high school reunion hoping to connect with an old crush, Gerald. When she gets there, she finds out that Gerald is now Geraldine. Notable because, unusually for this trope, Geraldine is played by transgender actress Candis Cayne and is also stated to be a lesbian.
• Neighbours introduced Mackenzie Hargreaves this way. She came to Erinsborough in search of her father, (who she hadn't seen since she and her mother left him years earlier because he couldn't deal with her transition) and was reunited with Yashvi Rebecchi, an old classmate who had known her as Michael at the time. Yashvi recognised her but couldn't place her, and a misunderstanding involving her father Shane, who had been friends with Mackenzie's parents, forced her to come out sooner than she would have liked. The Rebecchis have taken it pretty well so far.
• An old friend of Dan Fielding's is a trans woman in Night Court.
• Sense8: Nomi reunites with one of her old hacker friends who was unaware that she had transitioned. Bug is a little thrown at first and accidentally uses her deadname a few times but eventually grows past it.
• Star Trek: Deep Space Nine has this with the character Jadzia Dax, to be more specific, the Dax symbiote bonded to Jadzia. While Dax first appears to be a gorgeous woman, Commander Sisko keeps calling her "old man". This is a reference to Dax's previous host: a crusty old diplomat and cool mentor named Curzon. The reunion is played for laughs, as both already know that the gender change has happened, but in "A Man Alone", even Sisko expresses some discomfort knowing the man he once shared some Ruji twin sisters with is now a young woman. In "Blood Oath", a Klingon friend of Curzon's encounters Jadzia and is quite appreciative.
  Kor: Dax! My Curzon? After eighty-one years I find you a kyamo-looking woman! Kiss me!
  Dax: How about just a great big hug.
• Happens when Nick Driscoll meets a drop dead gorgeous woman at his class reunion in Stupid Stupid Man.
• One arc in Twin Peaks begins with Dale Cooper expecting the arrival of DEA agent Dennis Bryson, who he had worked with in the past. The coworker shows up at the Sheriff Department's office... as Denise Bryson. In a subversion of how this trope is usually played out, Dale himself is quickly accepting of her transition. Sheriff Truman simply expresses shock, while Deputy Hawk refuses to shake her hand and misgenders her behind her back.
• In Two and a Half Men, notorious womanizer Charlie is invited to a bar to meet up with an old girlfriend named Jill, only to find that his ex has transitioned and is now a handsome man named Bill (played by Chris O'Donnell). Although they become friends again, Charlie is quietly disturbed by the idea that he slept with a man and starts wondering if he's gay. Then Bill starts dating Charlie's mother.
  Alan: Do you realise what this 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!
• Daniel in Ugly Betty runs across this trope. A woman whom he hits on turns out to be his brother, whom everyone thought was dead and who has, post-faked death, undergone SRS.
• What Would You Do? used this trope as the basis for at least two episodes, featuring a transgender woman and a transgender man. In both cases, actors playing former acquaintances or classmates of the transgender people react with bigotry and bullying, with the intention of seeing whether bystanders will step in and put a stop to their behaviour.
• In an episode of WKRP in Cincinnati, Herb starts flirting with a woman who claims she knew him in high school. While making out with her, he learns he did know her in high school... before she had the operation. She was a teammate of his on the high school football team — the center to Herb's quarterback. To say Herb had a case of the Squick is putting it mildly.

Radio

• One BBC Radio comedy show subverts this. A man expecting a visit from an old male schoolfriend he hasn't seen in years is surprised when a woman shows up at his doorstep instead. When he awkwardly asks her when she "had the op", the woman gets confused and tells him she hasn't. She turns out to be a completely different classmate with the same first name as his schoolfriend, who has since gotten married and now has the same last name as well.

Video Games

• A variant in Baldur's Gate III. 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.
• Gabriel of Blood II: The Chosen is brought Back from the Dead when Caleb opens up a wormhole and retrieves him from a different dimension alive and well, but somehow turned from Gabriel into Gabriella:
  Caleb: Things have changed... but I don't need to tell you that.
• In 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.
• One of the protagonists of Xenoblade Chronicles 3: Future Redeemed is A, whose true identity is the masculine-presenting Alvis from the 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.

Webcomics

• Age Matters: In the final episode, Roan comes across a girl who is very invested in helping him get a gift for Rose and ignores all his attempts to ward her off. The girl shows up at the family reunion, and Roan realizes that she's Skye, Dylan's younger brother.
• While not exactly a "friend", Shay from Between the Lines (2006) comes across a girl who used to bully her as a little kid due to being feminine. Both are trans girls, which causes Shay to berate the girl for having been an Armoured Closet Trans person.
• Aubrey of Boy Meets Boy initially presents as a woman, but despite being introduced as Harley's best friend (whom Mik hates), drops completely off the radar for a long stretch. He reappears towards the end of the strip's run and Mik doesn't even recognize him at first.
• Childhood Friend Yuri During their eventual reunion at college, The Protagonist initially shocked that a girl who greets her is turns out to be her childhood friend, that she remembers as a guy. The Childhood Friend then explains casually that she hasn't done bottom surgery yet.
• In Dan and Mab's Furry Adventures, this turns out to be why Dan didn't recognize Biggs; he'd gone by "Bridget" the last time they met.
• Darkest Night: Nessa was Mags' friend as a child before transitioning much later. She'd told Mags about her gender dysphoria even then but they didn't meet again before Nessa had transitioned.
• El Goonish Shive: 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.
• '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.
• Least I Could Do didn't show Cyndi for a good long while, before a random man mentions the old joke of buying a horse a prostitute to Rayne and introduces himself as Carter. Becomes a Pet the Dog moment for Rayne as he keeps repeating Carter's new name to avoid accidentally deadnaming him.
• In Rain (2010), Gavin was best friends with Rain when she was called 'Ryan.' They went to separate schools and drifted apart, and when she transfers into his high school as a girl, he is immediately attracted to her, not (initially) recognizing her.
• The Sunjackers: Candy Chip meets her old teacher post-transition, and quickly corrects her when she's accidentally deadnamed.
• In Tales of the Galli, Emperor Constantine discovers that Katia the Battakes, who has come for a formal interview, is actually his old bodyguard Kasen, who is now a eunuch Galli.
• Transcendent features Olive, a trans girl, and her childhood friend Gigi who moved back to the area recently. What Olive doesn't realize is that Gigi had a massive crush when they were little, before Olive came out of the closet. As soon as Gigi lays eyes on Olive she's immediately smitten again.
• Tripping Over You: After getting a publishing contract, Liam meets up Matt, the one person he talked with in law school. Matt has since changed his appearance greatly and started his transition.
• An arc in Welcome to Room #305 has Yang Jooha trying to meet an old friend from high school. He tries to avoid her as he's living as a man now. When they meet face-to-face, he ends up dressing awkwardly as a woman, but they later meet normally. Yang Jooha has no issue with him being transgender, but their other school friends are less accepting.

Web Original

• In the Paradise setting, humans are randomly, permanently changed into Funny Animals by causes unknown — and sometimes gender-swapped at the same time — though the effects of these Changes are Invisible to Normals who will continue to see the Changed person as his or her old self (and gender). However, at one point a Ret-Gone effect kicks in for these gender-changed, with reality editing itself to reflect their new gender. As part of this, family members may be surprised to discover that photos of their brother or son now show their sister or daughter, even though their memories of said person's original gender remain intact. Also, those going through the Change themselves will start to see friends' or loved ones' new animal forms (and genders) in person, or in photos they happen to have about.

Western Animation

• In the Codename: Kids Next Door episode "Operation: C.A.R.A.M.E.L.", Numbuh Five helps her partner-turned-enemy-turned-friend Henrietta von Marzipan return to her true gender after being cursed to be a boy. This stabilizes their formerly tumultuous relationship, and Numbuh Five is shown to care about her greatly. Due to Values Dissonance, the rest of Sector V react in a horrified way after finding out she used to be their enemy.
• Family Guy:
  • The episode "Quagmire's Dad" runs with this trope. Quagmire's father has a sex change, and is now living as a woman named Ida. Ida goes to a hotel, meets Brian and has sex with him. Brian has heavy doses of Squick when he finds out Ida was Quagmire's dad, resulting in a Vomit Indiscretion Shot that is so long it Crosses the Line Twice.
  • When Stewie goes to the future in Stewie Griffin: The Untold Story, he finds out Meg has transitioned after college and is now a man named Ron. His only reaction is shock that Meg went to college.
• While it's not a plot point, there is an example in the Harvey Birdman, Attorney at Law episode "Droopy Botox" — at the end, Harvey walks into Phil Ken Sebben's office to tender his resignation, only to walk in on a surprise party for him. Heading the surprise party? Phil Ken Sebben, who's undergone gender reassignment and become a total bombshell (still with the eyepatch, though). Harvey asks, exasperated, "Do I know you people?" Then she speaks — and it's still Stephen Colbert's voice.
• Implied with Masha in The Owl House. Luz (who doesn't know them personally) refers to them in passing as "that girl" in "Yesterday's Lie", and they're definitively shown to be nonbinary "Thanks to Them". This discrepancy is never addressed, making it unclear if they transitioned during the several months between the two episodes (which is supported by their Vocal Evolution between the two points), if Luz accidentally misgendered them and Vee was simply too distracted from their current predicament to correct her, or if they had their gender retconned.
• Rocko's Modern Life: Static Cling: When Rocko and his friends track down Ralph Bighead, the original creator of the Fatheads, they discover that she's come out as a trans woman named Rachel.
• The Simpsons: In "Holidays of Future Passed", a future Lisa goes onto Facebook and sees that Martin Prince has now become "Marsha Princess". This is retconned in the Sequel Episode "Days of Future Future".

Real Life

• President George W. Bush surprised some former classmates with his handling of this situation at his Yale class reunion. A woman approached Bush, introduced herself, and said, "You may not remember me, but when I attended here, my name was Peter." Bush, according to reports, took her hand and shook it, and said "Now you've come back as yourself."
• During one of his shows, U.S. radio Shock Jock Doug "The Greaseman" Tracht received a call from a listener who, upon returning to his old hometown for a class reunion, met a beautiful woman who was formerly his good male friend. She wanted to go out for drinks; the caller asked if it would be "weird" to agree to a date. Greaseman handled the situation with surprising sensitivity, pointing out that at the very least, it would be two old friends touching base — and that if it turned into "something more", there was nothing weird or "gay" about it, because "he's a she now".

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