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 [[GayGroomInAWhiteTux 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; [[WhyWasteAWedding weddings are quite expensive to organise, after all.]]
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!!Examples:
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[[folder: Film -- Live Action ]]

* ''MadeOfHonor'' [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 ''MyBestFriendsWedding'', 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 SeltzerAndFriedberg's ''Date Movie'', where Grant's best man, [[TomboyishName Andy]], turns out to be his sexy ex-girlfriend as well. Julia finds this out the hard way.

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[[folder: Live Action TV ]]

* In ''Series/GilmoreGirls'', Rory was the best man at her grandparents' vow renewals.
* In ''Series/{{Dexter}}'', Debra is Dexter's best "man". She's his foster sister.
* In ''UglyBetty'', Bradford passes up his son Daniel as best man and instead asks his transsexual daughter Alexis to stand up with him.
* On ''Series/BuffyTheVampireSlayer,'' Xander picks Willow as his best "man". Of course, her being a woman does not stop her from [[LipstickLesbian flirting with one of the bridesmaids]]. She does try to use it as an excuse to get out of her [[ImpossiblyTackyClothes 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 ''Series/NightCourt'', Bull has Roz, his best friend, play this role at his wedding.
* On ''Series/GeneralHospital'', 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 ''Series/{{NCIS}}'', the person Palmer has tapped to be the best man at his wedding was Abby. [[spoiler: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 ''Series/{{Cybill}}'', when Ira is getting remarried, he asks Cybill (his ''ex-wife'') to be this for him.
* On ''Series/{{GreysAnatomy}}'', Alex asks Meredith to be his best man for his wedding with Izzie.
* ''Series/{{Seinfeld}}'':
** 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.

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[[folder: Music Videos ]]

* In the video for KatyPerry's "Hot 'n' Cold", one of the bridesmaids is a grubby, stubble-faced man.

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[[folder: Webcomics ]]

* The tomboyish lesbian friend of the male lead of ''MarryMe'' is his best "man" in the epilogue.
* In ''GirlsWithSlingshots'', most of the groom's friends are women, so during the wedding, we have a train of "groomsmaids".

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[[folder: Web Original ]]

* The "male bridesmaid" version of this has 214 story examples (and counting!) at [[http://www.fictionmania.tv/search/keywordsearch.html FictionMania]]. Invariably, the male lead [[WholesomeCrossdresser is required to wear clothing appropriate for the bridesmaid's role]].

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[[folder: Western Animation ]]

* In the season 2 finale of ''WesternAnimation/MyLittlePonyFriendshipIsMagic'', Twilight Sparkle's brother Shining Armor asks her to be best mare at his wedding.

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[[folder: Video Games ]]

* In ''VideoGame/TheSimsMedieval'', 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.
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