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Anime And Manga
- Sailor Moon has Luna, who was Usagi's guardian even way back during the Silver Millennium. Now, she also acts as advisor, much to Usagi's constant dismay.
- In Code Geass, when Nunnally returns to Britannia, they stick an overbearing, anal Maid, Miss Alicia Romeyer, on her, as a combination of Matron Chaperone and The Political Officer.
- Strawberry Shake Sweet has Julia, the plucky Teen Idol, and Saeki, her manager. Saeki is a kind of surrogate mother to orphaned Julia, but she's also constantly blocking Julia's advances towards her kôhai Ran.
- In Kasei Yakyoku, the Spirited Young Lady Akiko Hashou is the Maiden while the servant Sara Uchida is the Maid. Both get intolved in a Love Triangle with the Knight in Shining Armor Taka Itou. And things go From Bad to Worse very soon.
- The ages are inverted in Aldnoah.Zero, with Token Mini-Moe Eddelrittuo serving as handmaiden to the teenaged Princess Asseylum.
- In Card Captor Sakura, Tomoyo has four women as bodyguards. They are Author Avatars.
- Disney Animated Canon / Disney Princess
- Sleeping Beauty kicked off the Disney universe with a bit of a subversion. Aurora was the Maiden, but the role of The Maid was split between three fairies Flora, Fauna, and Merryweather. Future examples play it much straighter.
- Cinderella: The Fairy Godmother is the Maid who helps Cinderella, The Maiden. She's Older and Wiser, rounder, and by way of being a Magical Guardian is 'in the service' of Cinderella. The Fairy Godmother also gives her a sweet ride to the Ball behind the Evil Stepmothers back, and the iconic dress and shoes that entice Prince Charming.
- Robin Hood: In perhaps the most straight-forward example of all, Lady Cluck is the Maid to Maid Marion's Maiden.
- Beauty and the Beast: Mrs. Potts is the Maid to Belle the Maiden. She plays matchmaker in to break the curse. Technically she's actually Beast's servant, but gives Belle motherly support at the castle.
- Pocahontas: Grandmother Willow is the Maid to Pocahontas, The Maiden. Willow's a spirit that helps everyone who comes her way, but does try to steer Pocahontas from her intended in favor of John Smith.
- The Princess and the Frog: Grandma Odie is the Maid who helps Tiana The Maiden. She tries to get her together with Naveen as soon as they meet, and even marries them at the end. Despite being a little crazy, her role is a mix of the previous three Maids, being a helper to everyone in her realm like Willow, a matchmaker that breaks a curse like Potts, and a magical old lady that teaches tricks and gives gear like the Fairy Godmother.
- The princess in The Court Jester has Griselda, an older maid/companion who is a hypnotist.
- The Princess Diaries: Mia as the young princess-in-training and her grandmother the Queen who is overseeing it.
- Dot the robot (Maid) and Princess Vespa (Maiden) in Space Balls.
- Shakespeare in Love: Paralleling Romeo and Juliet, Nurse is a confidante and Secret Keeper for her mistress, Viola.
- Despite her name, Maid Marian is actually The Maiden who is usually accompanied by an older Maid servant in most of the Robin Hood tales. In adaptations:
- Book 3 of The Faerie Queene: Britomart's old nursemaid Glauce is the one who suggests that Britomart go to Faerieland disguised as a knight to find Artegall, the knight she seeks, and Glauce accompanies her, disguised as her male squire.
- In Wyrd Sisters and Witches Abroad, Magrat Garlick is the Maiden while Granny Weatherwax and Nanny Ogg split the role of Maid. In the latter, this is subverted with Lilith, who acts the role of Maid to Ella but is actually exploiting her for her own ends.
- In All Men of Genius, it's assumed by many characters that this is the situation with Cecily and her governess Miriam, though in fact, Miriam isn't actually very old and is a lot less prim when she isn't under observation. She's in a relationship with one of the senior students at the Academy, and goes out drinking with him and his friends. This causes problems when another student notices and tries to blackmail her into letting him hook up with Cecily.
Live Action TV
- Romeo and Juliet: Trope Codifier, The Nurse is the Maid who plays Secret Keeper for Juliet the Maiden as she tries to get with Romeo.
- Most Romeo and Juliet retellings, such as West Side Story, will have this dynamic also. West Side Story features Anita, who is only a few years older than Maria but quite a bit more mature and experienced (as well as Maria's older brother's girlfriend).
- The Merchant of Venice: Nerissa is the Maid to Portia's maiden. They both even go undercover together as men and keep the same dynamic. Nerissa is also officially Portia's waiting maid.
- Beatrice's relationship with Hero in Much Ado About Nothing is somewhere between being the Maid and being a Cool Big Sis. Beatrice is slightly older than Hero and has a big-sisterly relationship with her. Beatrice also gives Hero some relationship advice and tries to protect her when Hero is slandered. The big difference is that Beatrice has her own plot rather than just being a side-character in Hero's.
- The Legend of Zelda: Fulfills the imagery with Impa as The Maid and Zelda as The Maiden. In some incarnations Impa totally fulfills the stereotype by being much older and portly and is officially Zelda's attendant. In other versions she's a Ninja Maid since the series is in the Action Adventure Genre. The romantic element if any is only hinted at here.
- Elderly, wise Wynne from Dragon Age: Origins is this to the Warden. She frequently dispenses advice on life and love, and provides a forum for the Warden to brood about The Chains of Commanding.
- In Umineko: When They Cry, Jessica often talks about her love life and other woes to her servant and friend Shannon, who has a boyfriend (Jessica's own cousin George) while she doesn't. She is also the only one to know that Jessica loves Kanon, another servant, which her parents certainly wouldn't approve of (though she only knows this because she and Kanon are the same person). Played with a little in that Shannon is only more filled out in certain places, and though she's around the same age and not unattractive she Can't Have Sex, Ever.
- Depictions of Judith beheading Holofernes (most famously those by Gentileschi and Caravaggio) usually show Judith accompanied by her maid, as in the Bible story.