In a normal movie 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 girl? Or the bride is a tomboy who hangs out with all guys? This trope describes the events and confusion when you have a role that traditionally (and only traditionally) is one sex, being filled by the other. A gay wedding can be expected to have all sorts of such confusion (if even the "bride" is male, all bets are off). Doubly so when you consider that allegedly, the "best man" was supposed to step up to the plate in case the groom lost his nerve and ran for it; weddings are quite expensive to organise, after all.
- 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.
- 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 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 acts as "best man".
- In Gilmore Girls, Rory was the best man at her grandparents' vow renewals.
- In Dexter, Debra is Dexter's best "man". She's his foster sister.
- In Ugly Betty, Bradford passes up his son Daniel as best man and instead asks his transsexual daughter Alexis to stand up with him.
- On Buffy the Vampire Slayer, 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?Buffy: No.Willow: Oh. [pouts]Buffy: That would be totally unfair. We must share equally in the cosmic joke that is bridesmaids-dom.
- On Night Court, Bull has Roz, his best friend, play this role at his wedding.
- 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.
- 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.
- On Cybill, when Ira is getting remarried, he asks Cybill (his ex-wife) to be this for him.
- On GreysAnatomy, Alex asks Meredith to be his best man for his wedding with Izzie.
- 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.
- 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).
- In the video for Katy Perry's "Hot 'n' Cold", one of the bridesmaids is a grubby, stubble-faced man.
- The tomboyish lesbian friend of the male lead of Marry Me is his best "man" in the epilogue.
- In Girls with Slingshots, most of the groom's friends are women, so during the wedding, we have a train of "groomsmaids".
- 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 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.
- 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.