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- 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 he 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 cheerfully embrace.
Anime & Manga
- Subverted 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.
- Happened to Yukari in Family Compo. It's Played for Drama: one of her female classmate used to have a feeling for Yukari when Yukari lived as a man, and now that said classmate's marriage is in ruin, she lament 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.
- Although the two don't spend any actual time parted, Asuta Soro struggles with his growing attraction to his friend Hazumu in Kashimashi: Girl Meets Girl.
- The premise of the manga No Bra.
- 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 was a class reuninion but Yuki refused to go, averting this situation.
- 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 to them they start ambushing her with questions and making her uncomfortable.
- 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 women learns for herself who Aoi is when she notices her basketball skills (golf in the manga).
- 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.
- 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.
- 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 as an Elegant Gothic Lolita wearing woman.
- 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.
- Akane from Bokura no Hentai had known about Marika's desire to live as a girl for years however 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.
- Inverted in an old Doctor Fate comic, where a character takes most of a page to notice that the previously male Dr. Fate is a woman. (Since this version of Dr. fate was a man & woman fused into one, and the character in question was the human incarnation of a godlike Lord of Order, this actually made some sense, but was still played for laughs.)
- In the first chapter of You Got HaruhiRolled!, Kyon meets an attractive girl. Turns out she's Koizumi, frequent source of Ho Yay in the source material. Hilarity Ensues.
- 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?”
- The fundamental premise of Different for Girls.
- 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.
- One classic Filipino film, Miguel/Michelle, had 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.
- 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).
- In Pedro Almodovar'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.)
- Lois McMaster Bujold's 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 Dan Fielding's is a trans woman on Night Court.
- An old friend of Finch's is outed as a trans woman on Just Shoot Me!. She was played by Jenny McCarthy and Finch had a difficult time dealing with his attraction to her.
- Kristy McNichol played Gopher's former college roommate on an episode of The Love Boat.
- 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.
- Daniel in Ugly Betty runs across this trope. A woman whom he hits on turns out to have be his brother, whom everyone thought was dead and who has, post-faked-death, undergone SRS.
- Inverted in Two and a Half Men. 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.
- 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 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.
- 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.
- 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.
- The Jeffersons had an episode where George met up with his old Navy friend Eddie and found that she was now Edie. This was in 1977, a surprisingly sensitive early use of a trans character (and a black one at that). Of course it had the George-freaks-out-initially-but-learns-to-accept-it storyline.
- Happens when Nick Driscoll meets a drop dead gorgeous woman at his class reunion in Stupid Stupid Man.
- 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.
- 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 midly.
- 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.
- 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.
- A skit Israeli skit show Ktzarim showed a class reunion in which every member who used to have a nickname related to what they were known for 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.
- 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.
- Inverted on Sense8. Nomi reunites with one of her old hacker friends who was unaware his old friend Mike had become Nomi.
- Doctor Who: At the end of the series 8 episode "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 could change sex when they regenerate and this was the first onscreen example. The Doctor is shocked that the Master is alive, not that the Master is female. And then the Doctor's 13th regeneration ended up being female.
- On the Soap Opera The City (a Spin-Off of Loving, 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 a transsexual. It was the male version of her who'd had the crush on him, developed after he protected him from bullies.
- Community referenced 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 Abed was mining his life for classic sitcom plots.
- In Rain, 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 recognizing her.
- 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 later they meet normally. Yang Jooha has no issue with him being transgender but their other school friends are less accepting.
- 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.
- While not exactly a "friend", Shay from Between the Lines 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.
- 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.
- The Family Guy 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 not once, not twice, not three times, but FOUR times.
- While it's not a plot point, there is an example in the "Droopy Botox" episode of Harvey Birdman, Attorney at Law - 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.
- In The Simpsons episode "Holidays of Future Passed", a future Lisa goes onto Facebook and sees that Martin Prince has now become "Marsha Princess". Retconned in the sequel episode.
- 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."
- Stephen Colbert makes a very attractive woman when in drag. In fact, when he showed one of his brothers this picture, his brother expressed an interest in "her", giving this trope an extra dimension of Squick above and beyond the usual.