In a traditional Western wedding you have the bride, the groom, the best man, and the maid of honor, along with various groomsmen and bridesmaids. But what if the groom's best friend is a woman or his twin sister? Or the bride is a tomboy who hangs out with all guys or wants to include her Gay Best Friend?
This trope describes the events and confusion over wedding attendant roles filled by the opposite gender than usual. They're often given titles like best woman, man of honor, bridesmen, etc. It's increasingly becoming Truth in Television, as it's become more accepted for people to have close friends of the opposite gender, and for weddings to break from tradition.
What do they wear, you might ask? A woman on the groom's side will either wear the exact same suit as the guys, a pantsuit, or a business skirt with a blazer. If she absolutely must wear a dress, it'll be the same color as the suits, but simple and modest enough to not draw too much attention away from the couple. A man on the bride's side will wear a suit that's either the same color as the bridesmaids' dresses, or is a neutral tone while the shirt or tie is that color. Along with it, he'll either wear a boutonniere matching the bridesmaids' flowers, or just go all in and hold a bouquet like the ladies.
A gay wedding can be expected to have all sorts of such instances, due to the prevalence of fag hags, lez bros, non-binary people, etc. At the very least, same-gender weddings with mixed-gender wedding parties are less likely to draw criticism from traditional-minded family members than their hetero counterparts, as someone who's that concerned about tradition would likely not attend in the first place.
- At the wedding of Apollo and the Midnighter, The Engineer (Angela Spica) is attendant to the black-tux-clad Apollo.
- In the NCIS fanfic "Shards to a Whole", Palmer was a male bridesmaid for Abby when she married McGee, repaying Abby for being his Best Woman when he married Breena (see Live Action TV below).
- In the My Little Pony: Friendship Is Magic fanfic "Wedding of the Millennium", Discord asks Fluttershy to take on this role in his wedding to Celestia.
- In an ER fanfic featuring Doug and Carol's wedding, he asks a female friend of his to be his "best man", while she asks his former best friend (but now hers) Mark to be her "best man", as (a) they want a small wedding sans a large bridal party, only with the two witnesses necessary, and (b) they cite what good friends each of these people has been to them over the past year.
- “Different manor” invokes a non-wedding version of this in Harry Potter’s relationship with Daphne Greengrass. As part of her Power Dynamics Kink, Daphne takes pleasure in establishing her authority over Harry, but proclaims herself to be his master rather than his mistress, as she feels that “mistress” suggests she’s just the woman Harry’s cheating on his wife with when she intends to be his one and only wife.
- "we'll bury these old ghosts here" looks at the characters of Brooklyn Nine-Nine in the aftermath of the Snap (Avengers: Infinity War). With only Holt, Jake, Rosa and Charles left of the main cast, when Charles gets married a few years after the Snap he finds himself short on male friends to act as groomsmen aside from Jake. Since asking Holt to just be a groomsman after he officiated Jake's wedding would feel like it would be slapping the captain in the face (and asking Holt to perform the ceremony here doesn't work as Holt has no real connection to the bride), Jake suggests that Charles ask Rosa to be a groomsman, and she accepts the offer.
- Nora takes this position for Jaune in The RWBY Loops. She realizes only too late that as Jaune and Pyrrha are having a klingon-style wedding, she will have to fast for a week. This is, of course, played for laughs.
- In Father Goose, Cary Grant is stranded on an island during World War II with schoolteacher Leslie Caron and seven female students. Grant and Caron fall in love, and at the end of the film they are married while under fire from the Japanese and with the minister officiating by radio. The most tomboyish of the students, "Harry"note , acts as "best man".
- Four Weddings and a Funeral. Charles' friend Scarlett is wearing a tuxedo at his wedding (though with a pink shirt instead of white), indicating that she's serving as one of his groomsmen.
- Made of Honor [the Patrick Dempsey movie] is about a male bridesmaid. It's mentioned in the film, too, that if he had gotten married first, the bride would have expected to be his best man.
- Similarly, in My Best Friend's Wedding, the groom's father mentions to Julianne that he had suggested that groom make her his best man, but the bride-to-be wanted her for her maid of honor.
- Happens in Seltzer and Friedberg's Date Movie, where Grant's best man, Andy, turns out to be his sexy ex-girlfriend as well. Julia finds this out the hard way.
- In Sorcerers, Alyona invites her coworker and good friend Kivrin to be the bride's man at her wedding.
- In The Rook, a non-wedding version of this is mentioned in Myfanwy's notes on the history of the Checquy organization. Due to the habit of naming the main leaders of the Checquy "Lord" and "Lady", at one point the only valid candidate for the title of "Lady" was a six-foot-tall mountain of a man with a thick red beard who stubbornly held onto his position even when he had the chance to become the new Lord instead, remaining the Lady until his death.
- In a Blackadder episode when Blackadder is getting married, his bride-to-be doesn't have any female friends, so Baldrick fills in as her maid of honor.
- In the Buffy the Vampire Slayer episode "Hell's Bells", Xander picks Willow as his best "man". Of course, her being a woman does not stop her from flirting with one of the bridesmaids. She does try to use it as an excuse to get out of her horrible bridesmaid dress, though.
Willow: I'm supposed to be best man. Shouldn't I be all ...Marlene Dietrich-y in a dashing tuxedo number?
Willow: Oh. [pouts]
Buffy: That would be totally unfair. We must share equally in the cosmic joke that is bridesmaids-dom.
- On Castle, Ryan and Esposito spend an episode competitively sucking up to Castle to try to be his best man. At the end of the episode, he reveals that they're both welcome to be groomsmen, but his best "man" is definitely going to be his daughter. Then the wedding gets eaten by an end-of-season cliffhanger, so it becomes irrelevant...
- On Cybill, when Ira is getting remarried, he asks Cybill (his ex-wife) to be this for him.
- In Dexter, Debra is Dexter's best "man". She's his foster sister.
- On General Hospital, Brenda served as both the best "person" and maid of honor at Ned and Lois' wedding, being the best friend to both of them.
- In Gilmore Girls, Rory was the best man at her grandparents' vow renewals.
- On Grey's Anatomy, Alex asks Meredith to be his best man for his wedding with Izzie.
- On NCIS, the person Palmer has tapped to be the best man at his wedding was Abby. Unfortunately, because they were busy with the Harper Dearing case, the only person at NCIS other than Palmer who actually got to attend the wedding was Ducky.
- She gets to fill this role for McGee when he marries Delilah at the end of Season 14—with Gibbs as the "man-of-honor"!
- Modern Family: Claire is "Best Person" at Mitch and Cam's wedding, something she joyfully puns on in her after-dinner speech. Meanwhile, Cam's sister Pam is (initially) dressed identically to Claire and seems to be fulfilling the same role for Cam's side of the family, but they're never referred to collectively as either "bridesmaids" (since there's no bride) or "groomsmen" (since they're both women).
- On Night Court, Bull has Roz, his best friend, play this role at his wedding.
- On Parks and Recreation: April Ludgate asks if she can be Ron Swanson's best man when he marries Diane Lewis. He agrees and lets her.
- In The Rookie (2018) episode "Man of Honor", Detective Angela Lopez asks Sergeant Tim Bradford to be 'Man of Honor' at her wedding as her current maid of honor is too controlling, where Bradford is able to make a stand and help Lopez find what she wants rather than what others think will work best.
- On Schitt's Creek Stevie serves as the "Maid of Honour" for both Patrick and David and she wears a suit to the wedding.
- On Scorpion, when Toby and Happy are getting married, Toby asks Paige to be his "best ma'am", while Happy gets Walter, Cabe, and Sylvester to be her "dudes of honor".
- Elaine wants to be an usher at George and Susan's wedding. Susan objects to having a female usher. It turns out to be a moot point because somebody dies.
- This trope is discussed in another episode, where Elaine informs the others that she's the best man in a lesbian wedding, prompting George to ask how they decide who gets to be the bride and who gets to be the groom.
- Subverted in 30 Rock, Liz was supposed to act as best man in Jack's wedding to Avery, however, because the pastor couldn't speak English, he thought she was the bride, leaving her and Jack legally married for several days.
- In Ugly Betty, Bradford passes up his son Daniel as best man and instead asks his transgender daughter Alexis to stand up with him.
- Wings. Helen asks Joe to be her maid of honor when she gets engaged to Davis. They end up marrying.
- In the video for Katy Perry's "Hot 'n' Cold", one of the bridesmaids is a grubby, stubble-faced man.
- In Hamilton, one example that's unorthodox even for this trope is the wedding of Alexander and Eliza; Hercules Mulligan serves as the "flower man."
- In The Sims Medieval, the "Wedding" quest has two roles for Hero Sims, the Groom or Bride and a Best Man/Maid of Honor. (You choose the Sim the groom/bride marries, but don't control them.) The two roles can be played by two Sims of the same sex, or of opposite sexes.
- In Girls with Slingshots, most of the groom's friends are women, so during the wedding, we have a train of "groomsmaids".
- The tomboyish lesbian friend of the male lead of Marry Me (Bobby Crosby) is his best "man" in the epilogue.
- In Rhapsodies, Mr. Large Hideous Bull Creature invite's Dielle to be this. Dielle misunderstands and assumes he means Maid of Honor, and Large Hideous Bull Creature, who doesn't quite understand the concept, takes her word for it.
- The "male bridesmaid" version of this has 214 story examples (and counting!) at FictionMania. Invariably, the male lead is required to wear clothing appropriate for the bridesmaid's role.
- In The Nostalgia Critic's episode on Alvin and the Chipmunks: Chip-Wrecked, he has to attend Hyper Fangirl and Devil Boner's wedding as Hyper's "butler of honor".
- The Gayle episode "The Wedding" establishes that Bonnie was Gayle's Best Woman when she married Dave in 1986. Title aside, the role wasn't recognizably different from that of a traditional Maid of Honor, with Gayle's Insistent Terminology on the point apparently stemming from her feminist leanings.
- In the season 2 finale of My Little Pony: Friendship Is Magic, Twilight Sparkle's brother Shining Armor asks her to be best mare at his wedding. She hadn't known he was getting married in the first place and was not happy with being kept out of the loop.