The duenna (or chaperone) is a Stock Character whose main purpose is to provide an obstacle to the male Love Interest. Almost always a comedy character, she is older than her charge and intent on protecting her from the debauched hordes of unmarried men who (according to the chaperone) are waiting around every corner. Said young ladies are as anxious to get rid of her as her suitors. May also be an Old Retainer.
Usually a devout older woman who may be very naive about the world, though a common variation is one who has had a very eventful life, and thus knows exactly what to expect from young men.
- Dot Matrix from Spaceballs has this as one of her functions, even if she's actually not older than Princess Vespa.
Dot: That was my Virgin Alarm. It's programmed to go off before you do!
- Cyrano de Bergerac: Roxanne's chaperone is actually named Duenna.
- Done as a Running Gag in Robin Hood: Men in Tights (Mel Brooks seems to like this trope), which has Maid Marian's guardian, Broomhilde, repeatedly foil Robin's attempts to score with Marian. One instance has Robin blow a kiss, but Broomhilde promptly snatches it out of the air before it can reach Marian. And this one:
Broomhilde appears suddenly and prevents a kiss between Robin and Marian.
Robin and Marian sigh and roll eyes.
Broomhilde: (sternly) "No ding-ding without the wedding ring."
- Occasionally referenced in the works of Robert A. Heinlein. If they're set before World War II, then chaperonage was an issue to be confronted.
- In William Hope Hodgson's Carnacki the Ghost-Finder short story "The Horse of the Invisible," while Beaumont and his fiancee Miss Hisgins are together, they're chaperoned by her aunt.
- In Heidi, Fräulein Rottenmeier's role seems to prevent the title character (who is a rather adventurous 5-year-old) from having too much influence on her ward Klara, who is very frail.
- In Airborn, Ms. Simpkins fits this to a tee; she's not very brave, tries to keep her charge Kate from doing anything fun, and is especially suspicious when any young men are around.
- 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.
- Subverted in Sorcerer To The Crown: Prunella wants to travel to London with Zacharias. Her guardian would not allow this without a chaperone, so Prunella creates a kind of golem out of old clothes and illusions to give the impression that there is an older maidservant who will travel with them. There is no need for an actual chaperone, as Zacharias isn't a rapist (as is stated in an earlier scene when Prunella is alone with him, the thought would not even enter his mind), and Prunella is a practical-minded woman who wouldn't do anything that would damage her future.
- Briefly mentioned in early chapters of Beauty: A Retelling of Beauty and the Beast; Beauty remarks that once her eldest sister Grace is engaged, she stops wanting to go to parties and things, so their middle sister Hope has to go in the company of their chaperone, "the last of our outgrown governesses".
- In the A Memoir By Lady Trent series, the eponymous Lady Trent has to have a female companion everywhere she goes to avoid scandal for being an unmarried woman in the company of men, even though she's a widow with a son. Subverted in that her "chaperones" are just as annoyed by it as she is and her Love Interest cares about her far too much to risk scandal. She ends up getting married primarily because the travel accommodations got too complicated for her companion to go on an expedition with her, so she married Suhail to make it "proper".
- Star Trek: The Next Generation episode "The Dauphin": Salia, the future queen of Daled IV, is accompanied by her governess Anya, who is very protective of her. When Wesley is attracted to Salia and they get together, Anya turns into a giant monster and breaks into Wesley's cabin to stop them.
- In one episode of The Golden Girls, Blanche is uncomfortable about having made a date with a man in a wheelchair, so to avoid intimacy she takes Sophia along, claiming that she is her grandmother and chaperone.
- Ruy Blaz: A minor character shows up to tell the queen that while the queen is out hunting, she is not allowed to dance, eat sweets or basically enjoy herself. The pastiche movie La Folie des Grandeurs expands this character quite a bit, by making her think Ruy Blaz is secretly in love with her. Hilarity Ensues.
- One story by Jean De La Fontaine concerns a wife escorted by a chaperone, which greatly limits her extraconjugal affairs.
- The Nurse in Romeo and Juliet is an early subversion (or perhaps inversion). While she is Juliet's guardian and a concerned party in her romantic affairs, she's also a Reasonable Authority Figure who quite quickly becomes convinced (after meeting him) that Romeo is actually good husband material, and subsequently encourages Romeo and Juliet to be together. She's also a bawdy old woman who regales Juliet with tales of the sex jokes her late husband used to tell. It's possible she's supposed to be a parody of the more familiar "stern and overprotective" version of the stock character, and her unusual willingness to encourage her ward's romance (which, of course, doesn't end well) is part of the joke.
- Cyrano de Bergerac has a character named Duenna who, predictably, is Roxanne's chaperone.
- The Drowsy Chaperone has the titular Chaperone, who is the Chaperone of Janet, the bride-to-be. It's somewhat of a subversion, as the Chaperone isn't there to prevent Janet from seeing many men, but just one (the groom, Robert), and is actually more interested in sexual relationships than Janet is.
- This is a plot point in Charley's Aunt; Charley and Jack want to confess their love and propose to Amy and Kitty, but they can't be alone with the girls due to impropriety. Charley's aunt is expected to arrive at any moment to chaperone the four of them. When she's delayed, however, they draft one of their buddies to pretend to be her, since he's already in drag for a play.
- In Double Homework, when Rachels mom finds out that shes dating (and sleeping with) the protagonist again, she insists on supervising their joint training sessions afterwards, at least for a time.
- In Drowtales, Lady Ariel's slave Vaelia assigns herself the role of Duenna (Ariel is a shapeshifter). Also played with in that Ariel doesn't exactly want the attentions of her male suitor either, and is too young to really understand what he's trying to do to her.