Something's Different About You Now

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 transgender 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.

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.

Anime and Manga

 * 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.
 * 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.

Comic Books

 * 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.)

Film

 * Film example: Different for Girls.
 * During the slide show in National Lampoon's Class Reunion, it's revealed that a person from their class who'd never taken gym is now a housewife in another state. It's unspecified whether this student was a crossdresser then or is transgender now.
 * 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.
 * The 2014 film Boy Meets Girl comes close to this trope. It's about a fellow named Robby Riley (Michael Welch), who finds himself being forced to acknowledge his feelings for his longtime childhood friend, transwoman Ricky Jones (Michelle Hendley), which had been hidden below the surface for years.

Literature

 * 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 floweres in hand hoping to restart his old relationship with Lady Donna Vorryuter. He knew she went to Beta Colony concerning something involving the Succession Crisis surrounding her late brother Count Vorryuter, but it took several seconds for him to realize who that fellow accompanying the two Vorryuter 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.
 * 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 a female-to-male transexual and is Charlie's ex-girlfriend. This culminates in Charlie's mother Evelyn (briefly) dating this man.
 * 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 with 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 (Strictly Formula) 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, in fact 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 is now a she. Unlike most examples, this one is played by an obvious man in drag.

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

 * 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 an amusing real life example, Stephen Colbert himself could pull this off, as he resembles 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". The following explanation was probably awkward.
 * My... brain... Nothing is sacred anymore!

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."