It's an old archetype because in those days a woman going anywhere on her own was going to either a) have sex or b) be raped. The presence of a chaperone was intended to discourage the former and prevent the latter.
In this context, "Maid" doesn't mean "servant". It refers to more archaic connotations where it just implied an older woman. Hence the terms Old Maid and Fair Maiden. Still, The Maid may well be in the service of The Maiden, possibly as a Lady-in-Waiting.
The Maiden is more central to the story than The Maid. She may be The Ingenue, a Princess Classic, or a stubborn Plucky Girl. Basically a Female Hero appropriate for the time and place and audience. As such, expect her to be in a romantic plot.
The Maid will be the Maiden's confidante, sometimes a caretaker, older relative or just a good friend. If it is indeed a romance, The Maid will be the matchmaker, occasionally playing Secret Keeper if its a forbidden love. Alternatively The Maid will be a Matron Chaperone warning about the perils of rushing a relationship or blocking the male love interest.
If the Maiden's mother is also prominent, she'll usually be younger than the Maid and complete a Hecate Sisters ensemble with the other two.
Either because she's old, less attractive, or her own romances (if any) are less important, she's less desirable to the target audience. Has a tendency to be fatter than The Maiden also. But that doesn't mean she can't be a fan favorite, or to lack in gumption and spunk — she's sort of a prototypical Sassy Secretary.
Most common in romantic plays and musicals (and practically a requirement of any medieval romantic comedy) but the dynamic turns up in other mediums and genres too so they don't always have to be involved in a love story. If the characters sing, The Maid's voice type is either Mezzo or Alto, while The Maiden is a Soprano (usually an Innocent Soprano). See also Matron Chaperone.
- 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 Cardcaptor Sakura, Tomoyo has four women as bodyguards. They are Author Avatars.
- In Violet Evergarden, the 14-year old Princess Charlotte has Alberta, her lady-in-waiting. Unlike most examples of this trope which tend to ignore the maid's love life, the light novel specifically notes Alberta has been divorced twice.
- 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 straightforward example of all, Lady Cluck is the Maid to Maid Marian's Maiden. She explicitly describes herself as Marian's lady-in-waiting.
- Beauty and the Beast: Mrs. Potts is the Maid to Belle the Maiden. She plays matchmaker to break the curse. Technically she's actually the 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.
- Mulan: Grandma Fa is the Maid to Mulan's maiden, being more laid-back and aiding her granddaughter compared to her stricter parents.
- 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.
- Moana: Grandma is the Maid to Moana's Maiden, helping to steer her toward her destiny as The Chosen One of the ocean.
- The Last Unicorn: Molly plays the Maid to the Unicorn's/Lady Amalthea's Maiden. Molly is older and looks more unruly compared to the ethereal Unicorn. It's more prominent once she turns into a human girl. Played with, as the Unicorn is stated to be hundreds of years old, but as a human she mostly resembles a woman in her 20s.
- The Thief and the Cobbler. Princess Yum-Yum's Nanny is the Maid to the girl's Maiden. Nanny protects her from intruders and accompanies Yum-Yum in her dangerous adventures, even tackling desert ruffians who attempt (and fail) to ambush them.
- The princess in The Court Jester has Griselda, an older maid/companion who is a hypnotist.
- Ophelia: Gertrude and Ophelia initially have this dynamic; Queen Gertrude is an older woman who treats her young lady-in-waiting Ophelia like a daughter (which is unusual in that usually the younger woman is higher-ranking). It's partially Played for Drama, as Gertrude feels quite self-conscious about her looks now that she's getting older and feels she's less beautiful than her more youthful ladies, especially when an unwitting Hamlet unfavorably compares her with Ophelia/a younger woman. After Gertrude marries Claudius, she becomes more distant from Ophelia and even starts to blame her for Hamlet's behavior although they make up to an extent near the end, after Gertrude realizes Claudius is the real villain.
- The Princess Diaries: Mia is the young princess-in-training and her grandmother the Queen is overseeing it.
- Shakespeare in Love: Paralleling Romeo and Juliet, Nurse is a confidante and Secret Keeper for her mistress, Viola.
- Dot the robot (Maid) and Princess Vespa (Maiden) in Spaceballs. As well as being a loyal companion, she also makes sure Vespa isn't getting up to any hanky-panky before she's married, via her 'Virgin Alarm'; this proves to be a Moment Killer when Vespa and Lone Starr are about to kiss.
- 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:
- The Maid's name is Bess in The Adventures of Robin Hood. She's a likely inspiration for the character in The Court Jester example above.
- In Disney's Robin Hood, as noted above, Maid Marian's maidservant is a chicken named Lady Kluck.
- In Robin Hood: Men in Tights, her name is Broomhilde. She's usually sweet and caring, but has an uphill battle of making sure Maid Marion stays a Maiden.
- 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.
- In A Song of Ice and Fire, many highborn young ladies are entrusted to the care of a an older septa, who serves as a governess, tutor and chaperone. Sansa and Arya Stark have Septa Mordane, Margaery Tyrell has Septa Nysterica, and in Fire & Blood, the Good Queen Alysanne Targaryen had Septa Ysabel.
- In Naomi Novik's Spinning Silver: duke's daughter Irina has her old nurse, Magreta, as a constant companion, although since the one trying to assault Irina's virtue and safety is the tsar himself, she's unable to do much to protect her. Unusually for this trope, Magreta has several viewpoint chapters that reflect on her history of self-sacrifice on Irina's behalf, as well as her own separate subplot.
- The second series of Blackadder has Nursie, the old, doting nursemaid to the younger Queenie. She is very loyal to the queen, who is in turn loyal to her, as Nursie is just about the only person Queenie doesn't try to have executed.
- Game of Thrones: Septa Mordane fits the "maid" and is this trope more to the traditionally more maidenlike Sansa than to Arya; she acts as Sansa's governess and tutor, and is so loyal she gives up her life for her.
- In The Vampire Diaries, Bonnie has a close relationship with her grams and often seeks her out in times of crisis. Grams also acts as mentor when Bonnie's witch powers kick in.
- In Wizards & Warriors, Princess Ariel is attended by the loyal if decidedly dim Cassandra.
- 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 being 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 a Cool Big Sis. Beatrice is slightly older than Hero and has a big-sisterly relationship with her; they're actually cousins, but have essentially been brought up as sisters, since Beatrice was taken in by her uncle (Hero's father) after she was orphaned. 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 female 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.