History Main / LoverAndBeloved

* In Marvel's ''ComicBook/TheIncredibleHercules'', most of the Greek gods assume (incorrectly) Hercules and [[TeenGenius Amadeus Cho]] have this relationship. Amadeus always angrily corrects them.

* ''Series/FellowTravelers'': Hawkins Fuller teaches his younger lover Tim Laughlin about the political intrigue that occurs around Capitol Hill, and he also introduces Tim to gay bars as part of the latter's "education," as Hawk calls it. He even sounds paternal in episode 5 when he utters to Tim "I didn't raise [[AffectionateNickname my boy]] to be a soldier."

* ''Series/FellowTravelers'': Hawkins Fuller teaches his younger lover Tim Laughlin about the political intrigue that occurs around Capitol Hill, and he also introduces Tim to gay bars as part of the latter's "education," as Hawk calls it.

'''Administrivia/NoRealLifeExamplesPlease''' [[noreallife]] This includes any real person describing their own relationships, or their personal interest in such relationships, regardless of medium.

* In ''VideoGame/AtelierSophieTheAlchemistOfTheMysteriousBook'', Plachta is Sophie's ReallySevenHundredYearsOld alchemy teacher. Their relationship is extremely romantic in tone, especially after [[spoiler:Sophie uses her alchemy to give Plachta a humanoid body]]. By the end of the game, they're "looking forward to spending more time with each other." In the next game they're travelling to the Examination together, though by that time their relationship is one of equals, as Sophie has become a master alchemist in her own right.

** Note that all the in-canon references to this are nasty rumors being spread about the main characters, all of which are unfounded. Specifically Kouryuu and Koumyou's relationship is explicitly NOT like that despite the talkers. One of the things that makes the scene where a newly-crowned Sanzo leaves the temple and is nearly raped by bandits so poignant is his realization of how much his foster father had sheltered him from such things. Sanzo and Goku were probably intended to be a lot closer to this trope so the fangirls could squee, while not being quite as squicky as the pre-pubescent Kouryuu and middle-aged Koumyou. [[spoiler:[[DepravedBisexual Ukoku]] and Kami, the unfortunate slave boy he takes in as an experiment to see what Koumyou sees in Kouryuu, probably play this trope a lot [[IncrediblyLamePun straighter]], if about fifty times more disturbingly.]]

* This is the dynamic between Gulcasa and Nessiah in ''VideoGame/BlazeUnion'', where Nessiah plays the role of [[TheCaretaker caretaker]], [[LivingEmotionalCrutch confidant]], and [[MagnificentBastard kingmaker]] to the more inexperienced and emotionally vulnerable Gulcasa. Of note is the fact that while Nessiah is [[ReallySevenHundredYearsOld definitely much older]], the two are about the same age physically, and Nessiah is also the smaller and more delicate of the pair. Over time, the two of them shed this trope as Gulcasa becomes more emotionally dominant and Nessiah more dependent.

* ''Film/ReservoirDogs'' (1992) [[https://cinemalogue.com/2012/10/23/reservoir-dogs-retro/ has]] [[https://thesundae.net/2019/08/19/you-kill-that-man-you-die-next/ been]] [[https://scrapsfromtheloft.com/movies/reservoir-dogs-review-homosexual-subtext/ interpreted]] this way, given that a popular reading is that the relationship between Creator/HarveyKeitel and the younger Creator/TimRoth carries HomoeroticSubtext. In this case the "beloved" isn't what he seems, acting almost as a male FemmeFatale if you subscribe to the queer reading.

* ''Series/InterviewWithTheVampire2022'': In vampire terms, Lestat de Lioncourt is Louis de Pointe du Lac's maker (the vampire who turned him), and his express purpose for doing this is so that [[ILoveYouVampireSon Louis becomes his eternal lover]]. [[Recap/InterviewWithTheVampire2022S1E2AfterThePhantomsOfYourFormerSelf The second episode]] focuses on Louis' experience as a fledgling vampire with Lestat (who is much older than him) as his teacher in vampirism, while also being involved in what Lestat calls a "vampire romance."

* ''Series/InterviewWithTheVampire2022'': In vampire terms, Lestat de Lioncourt is Louis de Pointe du Lac's maker (the vampire who turned him), and his express purpose for doing this is so that [[ILoveYouVampireSon Louis becomes his eternal lover]]. The second episode focuses on Louis' experience as a fledgling vampire with Lestat (who is much older than him) as his teacher in vampirism, while also being involved in what Lestat calls a "vampire romance."

* The American version of ''Series/QueerAsFolk'' had this kind of relationship in the alpha couple after a while, although it didn't follow the classical formula of the older guy being the more enthusiastic.

* ''Film/ReservoirDogs'' [[https://cinemalogue.com/2012/10/23/reservoir-dogs-retro/ has]] [[https://thesundae.net/2019/08/19/you-kill-that-man-you-die-next/ been]] [[https://scrapsfromtheloft.com/movies/reservoir-dogs-review-homosexual-subtext/ interpreted]] this way, given that a popular reading is that the relationship between Creator/HarveyKeitel and the younger Creator/TimRoth carries HomoeroticSubtext. In this case the "beloved" isn't what he seems, acting almost as a male FemmeFatale if you subscribe to the queer reading.

*** The finale has [[spoiler:Jack]] become Leslie's new "associate" for purely financial motives (until a gust of wind carries the tiny man off a balcony and he inherits his fortune)

* In some interpretations, ''Theatre/TheMerchantOfVenice''. There's a lot of HoYay between Antonio and Bassanio and Antonio, who is somewhat older than Bassanio, guarantees a big loan so that Bassanio can marry, in the process putting himself at risk of death at the hands of Shylock, whom he despises for being a Jew. In some readings the relationship is seen this way: Bassanio has a good male buddy his own age, but his boyfriend is the older, richer man Antonio. The rather reckless, youthful Bassanio is sincerely fond of Antonio but is also well aware that he has Antonio wrapped around his little finger; he wheedles money out of him and then proceeds to go off with a girl. The self-sacrificing Antonio, who loves Bassanio more than Bassanio loves him, watches and even facilitates this, keeping a lid on his own private pain over his love for Bassanio. All this is classic Lover and Beloved. Other readings, however, see a fully mutual love affair between Antonio and Bassanio, with Bassanio marrying Portia largely for her money, though he does declare his love for her. Still, other readings see no sexual or romantic relationship between the two, with Antonio's love for Bassanio wholly unrequited, and yet others interpret Antonio and Bassanio simply as HeterosexualLifePartners.
* Also by Shakespeare, Achilles and Patroclus in ''Theatre/TroilusAndCressida'' probably are an example of this. At any rate, Thersites refers to Patroclus as Achilles' "masculine whore", and Patroclus is highly offended at the insulting choice of words but doesn't '''deny''' it.

* ''Über die Stufen von Marmor'' (''Above the Marble Steps''), a one-act play, one of John Henry Mackay's ''Books of the Nameless Love''. In Venice, a young German sculptor and a sixteen-year-old tourist, both male, discover that they are in love and, during a one-hour interlude with the stage curtain drawn, have sex.

* Joe Orton's ''Entertaining Mr Sloane''. A sister and brother in their thirties both have the hots for a young man of eighteen or nineteen. [[spoiler:They end up sharing him.]]
* Harold Pinter's ''The Confession'' is about two couples: James and his wife Stella, both in their thirties; and Bill, in his twenties, and his boyfriend Harry, in his forties. Stella and Bill are both dress designers and the plot revolves around a one-night stand they may or may not have had.
* Simon Gray's ''Butley''. The eponymous protagonist, who like Gray is a lecturer in English literature, is thoroughly unproductive at his job. He has recently married and had a daughter, but he and his wife separated after a short time together, and she tells him she's leaving him for another man. The same day, Butley's boyfriend also tells him that he's leaving him for another man. The boyfriend (with whom Butley [[ChastityCouple may never have had sex]], because Butley is not keen on being homosexual, which is also why he got married) is younger than Butley by ten years or so and used to be his [[TeacherStudentRomance student]]. Now he is a colleague, working as a lecturer in the English department of Butley's university and in fact sharing his office. The man he leaves Butley for is about his own age, which is late twenties, or if he's older it's not by much, but this man is clearly the dominant one in the relationship.

* In Julian Mitchell's ''Another Country'', which was made into a film of the same name, a boy at secondary school is deeply in love with a boy about a year younger and nobly protective of him.
* GenderInvertedTrope of this in one of Eve Ensler's ''Vagina Monologues'', "The Little Coochie Snorcher that Could". A 13-year-old girl who when she was younger was violently raped by a man is given vodka by a 24-year-old woman who then gently seduces her. She describes the experience as positive and concludes, "Now I'll never need to rely on a man." In response to the controversy this caused, Ensler later raised the girl's age to 16. [[DoubleStandardRapeFemaleOnFemale The girl adds defiantly that some people would call this rape, but "well, I say if it was rape, it was a good rape."]] Ensler removed this line, again because it caused massive controversy. Ensler herself was raped by her father as a child.

* In ''VideoGame/AtelierSophieTheAlchemistOfTheMysteriousBook'', Plachta is Sophie's ReallySevenHundredYearsOld alchemy teacher. Their relationship is extremely romantic in tone, especially after [[spoiler:Sophie uses her alchemy to give Plachta a humanoid body]]. By the end of the game, they're "looking forward to spending more time with each other." In the next game they're travelling to the Examination together, though by that time their relationship is one of equals, as Sophie has become a master alchemist in her own right.

* In Creator/{{Plato}}'s ''The Symposium'', one character opines that there ought to be a law against courting young boys, as opposed to older boys, because if a man goes after a young boy he is wasting his efforts on an uncertain prospect.

* ''Don Leon'', a long poem of anonymous authorship, published in 1866 but probably written in the 1830s. It is written in the first-person voice of Lord Byron and is a passionate defence of homosexuality, directed against the law forbidding sodomy. It describes Byron's love for various boys, refutes the notion that Sodom and Gomorrah were destroyed because their inhabitants practised sodomy, and makes reference to the Greek pederastic tradition, including to Creator/{{Plato}} and Socrates and to Epaminondas, who was a great Theban general and statesman and had a younger boyfriend, Cephidorus. Love between two boys or between a man and a boy is the only form of homosexuality mentioned in the poem; love between two men is not considered.
* ''The Romance of a Choir-Boy'', the story of Philip Luard, a young man studying to be a [[PedophilePriest priest]], who falls in love with Teddy Faircloth, a beautiful boy of twelve and a half. Recognising the exceptional beauty of Teddy's soprano voice, he arranges for Teddy to attend a famous London choir school. Two years later, when Teddy is fourteen and a half, the two have a friendship, Philip mentoring Teddy and resolving, in spite of his sexual attraction to Teddy, to keep the friendship on a chaste footing. The author, John Gambril Nicholson, a teacher at boys' schools, also wrote Uranian poetry.
* Frederick Rolfe's ''Stories Toto Told Me'', in which the Roman Catholic Don Frederico and his teenage acolytes walk in the Italian countryside and the head acolyte, sixteen-year-old Toto, tells stories about the saints, who in the stories behave more like pagan gods. These ''Toto'' stories contain pederastic elements; Corvo represents this as the 'Greek love' that all educated men of his time knew about from their reading of the Classics. In a later novel, ''The Desire and Pursuit of the Whole'', Rolfe presents a slightly disguised version of the trope. Nicholas Crabbe, a very Corvo-like figure from a highly autobiographical earlier novel, ''Nicholas Crabbe'', rescues a 16-year-old girl from the Messina earthquake and employs her as his assistant and gondolier. To avoid scandal, he has her [[WholesomeCrossdresser wear boys' clothes]]. Crabbe ends up getting a book contract which assures him a lot of money and declaring his love to the girl. Earlier, as a young man, Rolfe had written sentimental poetry about boys swimming naked, boy martyrs, and so on.
* Creator/OscarWilde's ''Literature/ThePictureOfDorianGray'', in which two somewhat older men fall hard for a very beautiful young man. Wilde also wrote a short story, ''The Portrait of Mr W. H.'', in which the main character is convinced, for various elaborately explained reasons, that the unknown "Mr W. H." to whom Creator/WilliamShakespeare's sonnets are dedicated was Willie Hughes, a boy actor, and that the sonnets to the "lord of my love", "lovely boy", "sweet boy", "master-mistress of my passion", etc. were written to him.
* ''The Priest and the Acolyte'', a short story by Oxford undergraduate John Francis Bloxam, who had also written a couple of romantic poems about boys. In the story, a 28-year-old Anglo-Catholic [[PedophilePriest priest]] and a 14-year-old acolyte (all acolytes were boys then, of course) fall in love with each other. The boy is the one who starts their relationship: he comes to the priest's room at night and confesses his love. They [[ChastityCouple don't have sex]], but they kiss and hug and at night they spend hours together in the priest's rooms, the acolyte sitting on the priest's lap. Their love brings them both happiness and helps them conduct Mass better too. Eventually another priest, the protagonist's superior, discovers them together, whereat the protagonist responds to this other priest's condemnation with a passionate defense of his own nature and his love for the boy. Afraid of the fallout, and wanting to be together forever, the priest and the acolyte commit suicide together by drinking poisoned Communion wine at a two-person Mass, said by the priest and served at by the acolyte, for the repose of their own souls.
* The Thomas Mann novella ''Literature/DeathInVenice'', which has Gustav Aschenbach falling hard for fourteen-year-old Tadzio and constructing an elaborate fantasy concerning this trope about him. He never does act on his feelings for him, but his refusal to leave Venice because of his desire for the boy leads to him contracting and dying of the cholera that is sweeping the city. Thomas Mann quotes from the ''Phaedrus'' in this.
* The 1990 novel ''Literature/LoveAndDeathOnLongIsland'' is an updated riff on ''Death in Venice'', but rendered less squicky and more humorous by the fact that the beloved is a TeenIdol actor in his early twenties.
* John Henry Mackay, along with his political writings, wrote the pederastic novel ''Der Puppenjunge'' (''The Hustler''). In the novel, a 15-year-old boy, Gunther, comes to Berlin from the countryside and becomes a hustler. Hermann, a young man working for a publisher, falls head over heels in love with Gunther, who at first doesn't care, and leaves him for a wealthy count who simply likes to watch Gunther lying naked on a bearskin. Gunther grows bored and returns to Hermann, who is deliriously happy, but then Gunther is picked up on the street and taken into care by the authorities. He escapes and comes back to Hermann, whom he grows to love in return. [[spoiler:Then they are discovered, Hermann is imprisoned for 'gross indecency', and Gunther is sent away to be a butcher's apprentice.]]

* E. F. Benson's 1916 novel ''David Blaize'', a [[OneGenderSchool boys']] BoardingSchool story. The title character takes up with Frank Maddox, three years older, who becomes his best friend, his (chaste) lover, his mentor, and protector. When David is new at school, according to custom he is Frank's servant. Later on, Frank has to beat David to teach him a lesson -- "this will hurt me more than it hurts you" kind of thing. David's open innocence 'redeems' Frank from the 'sin' of mutual masturbation with other boys.

* ''Les amitiés particulières'' (''This Special Friendship''), Roger Peyrefitte's classic novel set in a [[CorruptChurch Jesuit]] BoardingSchool [[OneGenderSchool for boys]]. Fourteen-year-old Georges has this kind of love affair with twelve-year-old Alexandre. Georges also has a friend his own age, Lucien, who's involved in a similar relationship with sixteen-year-old André. Georges and Alexandre remain chaste; Lucien and André do not. Georges looks up Greek and Roman pederastic poems, relating them to his love affair with Alexander; the [[PedophilePriest père de Trennes]], an archaeologist, talks about Greece, "where for once in the history of mankind, beauty and purity were united", and says that Georges should know about Greece, that he deserves to. The novel won the Prix Renaudot. Peyrefitte's much later, rather trashy novel ''Roy'' is about a thirteen-year-old boy prostitute who has a lot of sex, including sadomasochistic sex, with the rich men of Los Angeles, including the police chief.
* Invoked and subverted in Ursula Zilinsky's ''Middle Ground'', set in a Nazi work camp for male prisoners. The 33-year-old commander, Johannes von Svestrom, and a 16-year-old prisoner, Tyl von Pankow, fall in love. Tyl describes Svestrom as his "father, friend, lover and beloved". Svestrom later says that he does not believe love is possible except between equals. Svestrom has previously had a relationship with Tyl's uncle Gabriel, whose commanding officer he was; Gabriel, seven years younger than Svestrom, has been killed in action. Various of the camp guards have "favourite boys" among the prisoners. At least one of these relationships turns from exploitation into a committed mutual love. It begins when the boy prisoner is fifteen.
* ''Les Garçons'', by Henri de Montherlant, another tale set in a Jesuit school [[OneGenderSchool for boys]]. Relationships following this trope are common and accepted, even encouraged, among the boys. The heroic sixteen-year-old protagonist is very anxious to be a good mentor to his fourteen-year-old beloved, to the point of being willing to sacrifice the sex and even the relationship itself, and disapproves of the attitude of some of the other older boys, who are just in their relationships for the kicks.
* Marguerite Yourcenar's ''Mémoires d'Hadrien'' (''Memoirs of Hadrian'') deals, among other things, with the relationship between fifty-something Hadrian and teenaged Antinous.
* In Fritz Peters' ''Finistère'', published in 1951, one of the first mainstream novels with homosexual themes, a 12-year-old boy [[PrecociousCrush crushes]] on a grown man, a friend of his family. Then, when 15 and at a [[OneGenderSchool boys']] BoardingSchool, he has a [[TeacherStudentRomance love affair]] with a male teacher in his late 20s.
* Mary Renault's books, because she wrote a lot about ancient Greece, where this trope was the standard for homosexual relationships. In ''The Last of the Wine'', Alexias' lover Lysis is about 8 years older than him, which wouldn't be much except that they fall for each other when Alexias is 15 and start a relationship when Alexias is 16. In ''The Mask of Apollo'', Nikeratos is about a dozen years older than his life partner Thettalos, and the relationship starts when Thettalos is 18; Plato (yes that Plato) has an ongoing friendship with a man, Dion, whose lover he was when Dion was 20 and Plato was 40. In ''The Persian Boy'', 26-year-old Alexander the Great is seduced by 16-year-old Bagoas, which is the start of a 7-year relationship, lasting till Alexander's death. In ''The Praise Singer'', 15-year-old Harmodios embarks on a love affair with Aristogeiton, a man in his late 20s. ''The King Must Die'', ''The Bull from the Sea'', ''Fire From Heaven'' and ''Funeral Games'' don't feature this trope so prominently, but they all take place against the backdrop of societies in which young men, and sometimes older men, have relationships with teenaged boys and, if both are upper-class, are expected to mentor the boys. ''The Charioteer'', Renault's last contemporary novel, set during World War II, has its twenty-three-year-old protagonist Laurie involved in two relationships: he's the Lover to 19-year-old Andrew, the Beloved to 26-year-old Ralph. Incidentally, the teenaged Alexander and Hephaistion subvert this trope in ''Fire From Heaven'' by being a.) lovers and b.) the same age; this surprises Alexander's father Philip. However, these days historians think that relationships between adolescent coevals, albeit with a lover/beloved dynamic still obtaining, were probably common in ancient Macedon; each area had its own tradition of homosexuality. Bagoas, who comes from a different culture, sees Alexander as Hephaistion's "boy" and takes pride in giving Alexander the chance to play the "man's" role. Obviously, the Alexander/Bagoas relationship, the Harmodios/Aristogeiton relationship, and Plato's relationships with younger guys are fictional depictions of actual relationships recorded by history.
* ''Literature/{{Lolita}}'' is, of course, chiefly about a man sexually attracted to girls 9-14 years old and his passion for his 12-year-old stepdaughter, whose life he ruins. The homosexual version crops up with a minor character, a French expatriate named Gaston Grodin, who becomes friends with Humbert Humbert, the protagonist. Grodin is a professor of French at the local college. He and Humbert play TabletopGame/{{chess}} together (Grodin is a terrible chess player) and Grodin kindly gives Humbert various presents, surpluses from gifts given to him by the neighbourhood ladies -- he's popular in the neighbourhood. He also has a liking for young boys, which nobody seems to have noticed except Humbert. He keeps, and shows to Humbert, an album of snapshots of the local lads; in his basement, he has pistols and tiger-skins and other things likely to appeal to the boys, whom he invites round. Once, he and Humbert go to the theatre together, Humbert taking Lolita and Gaston taking a local boy, whose father is away that night. Humbert says that Grodin eventually got involved in a ''sale histoire'' (a nasty business), "in Naples of all places", and got into trouble.
* Sandro Penna's celebrated poems, which are largely about boys, since "everything else is uninteresting". In Penna's only collection of prose, there is a short story in which a man is attracted to a working-class boy of 12 or 13 whom the man sees in a barbershop.
* In Iris Murdoch's ''The Bell'', 40-year-old Michael falls in unrequited love with 18-year-old Toby and thinks that "...it might be possible to watch over him and help him...in a way that Toby would never know, in humble services obscurely performed at future times. ... He was conscious of such a fund of love and goodwill for the young creature beside him." While a 26-year-old [[OneGenderSchool teacher]], Michael had a brief, chaste [[TeacherStudentRomance love affair]] with a 15-year-old [[BoardingSchool pupil]] of his, Nick. This was the first time Michael had been attracted to someone so much younger than himself. He thought that "Nick, who was already his lover, would become his son"; indeed, Nick was "already playing both parts". But a revivalist preacher came to the school and after listening to his sermon Nick felt that his relationship with Michael was a sin, so he reported it, and Michael was thrown out of his job and his hopes of the [[PedophilePriest priesthood]] ended. In Murdoch's ''A Fairly Honourable Defeat'', two of the main characters, both grown men, one older than the other, are a lover/beloved couple. In ''The Nice and the Good'', a man becomes attracted to his 15-year-old nephew, who is oblivious, instead pining for a girl his own age. It later emerges that the man was thrown out of a Buddhist community somewhere in the East for having sex with an adolescent boy.
* Frits Bernard's two 1960 novellae. ''Costa Brava'' is about the love between a Venezuelan man and a twelve-year-old refugee boy during the Spanish Civil War. The man succeeds in reuniting the boy with his family; they lie to him, telling him the man has died, but years later the two meet again by chance and affirm their love for one another.''Vervolgde Minderheid'' (''Persecuted Minority'') is about a fifteen-year-old boy's love affair with his male {{teacher|StudentRomance}}; the man is imprisoned for the relationship and makes up his mind that on his release he will emigrate to get away from the Netherlands' legal and social condemnation of pederasty. Bernard was a psychologist and sexologist who campaigned for the acceptance of homosexuality and particularly pederasty.

* Lover / beloved affairs are also the done thing in ''Lord Dismiss Us'', another [[OneGenderSchool boys']] BoardingSchool story, from England this time. The trope is subverted in that sixteen-year-old Allen is more mature than eighteen-year-old Carleton, his boyfriend, the story's protagonist. Also, Allen comments, "With us it's different to everyone else. It's usually the older one who loves more. But I love you more." Twenty-four-year-old Ashley went to the school as a boy and there had a love affair with a younger boy, mirroring much of what is going on between Carleton and Allen, but has had no contact his former boyfriend since. He has now returned to the school as a literature teacher. Carleton wants to be a writer, and Ashley helps him with a story he is writing. Carleton has no idea about Ashley's affections and is initially shocked and repulsed when he finds out but softens his opinion later. Some other men among the teachers at the school are also attracted to the boys and have little coteries. Amusingly, the [[PedophilePriest chaplain]] has a taste for rather unwashed lads, whom he has to tea in his study. He keeps art of naked boys around, but never actually lays a finger on the real boys; their proximity is enough. He tells Allen, who wants to be a clergyman, that homosexual sex is a sin, but is fine with homosexual love. Carleton and Allen have independently decided to keep their relationship chaste. Carleton also remembers that when he was a small boy at his preparatory school, a teacher there used to sit on his bed and talk to him at night, sit Carleton on his lap, and touch Carleton's bottom.
* Angus Stewart's ''Sandel'' is about the love between Tony, a 13-year-old choirboy, and David, a 19-year-old undergraduate, who is reading English but is also an accomplished musician. David becomes a teacher at Tony's [[OneGenderSchool choir]] BoardingSchool. When 17 and at school himself, David fell in love from afar with a younger boy but never acted on his feelings. Tony is quickly growing up and the breaking of his voice, the growth of his pubic hair, the development of his adolescent coarseness of mind and manner will put an end to the boyishness that attracts David to him.
* At the beginning of Paul Scott's Raj Quartet, set near the end of the British Raj in India, Ronald Merrick, a policeman in his early thirties with repressed homosexual and sadomasochistic tendencies, becomes strongly attracted to a young man of 22. This young man is good-looking; he is stuck-up; he is Indian, whereas Merrick is white, and feels superior for it; he was raised in Britain, in a much more upper-class milieu than Merrick's, so Merrick feels inferior...it's a perfect storm. Merrick ends up ruining the young man's life. Someone else comments that Merrick "chose" Kumar because he was "unable to love. Only he was able to punish." In a later book, an older Merrick reappears, and it emerges that he has been sleeping with young Indian men. In between we meet Count Bronowski, an urbane elderly Russian who falls in unrequited love with young men; he recounts how he once loved an 18-year-old boy who loved a girl, and he is currently just as hopelessly in love with his young social secretary, Ahmed Kasim. There's also a rare gender-swapped version of the trope in which an aging lesbian falls in unrequited love with younger women. The trope is averted with Pinky, a 20-year-old gay man: he is frequently offered boy prostitutes on the street but "it wasn't a boy he wanted, but someone of his own age."
* Isabelle Holland's ''The Man Without a Face''. 14-year-old Chuck persuades 47-year-old Justin [=McLeod=] to tutor him over the summer so he can pass the entrance exam to a [[OneGenderSchool boys']] BoardingSchool, which will get Chuck away from his mother and older sister, whom he hates. Needing a father figure, Chuck becomes attracted to Justin, who mentors him, and Justin probably reciprocates the attraction, but Justin tries to keep things within strict bounds. It's hinted that when Justin was a teacher at the same boys' boarding school Chuck wants to go to, he may have had some sort of a relationship with a boy Chuck's age, who was killed in a car crash when Justin was drunk driving. Justin ended up in prison over this and feels deeply guilty about it -- both things for reasons not entirely spelled out.
* Subverted in Tony Duvert's ''Quand Mourut Jonathan'' (''When Jonathan Died''). An artist, Jonathan, has a four-year relationship with a boy, Serge, aged six to ten, twenty-one years younger than he is. Serge takes the lead in everything; Jonathan does whatever Serge wants. Jonathan is described as a "disciple" to the little boy, who sometimes sees Jonathan as being a child even younger than himself. The novel was inspired by a vacation Duvert had had with a neglected boy. Duvert's other novels also discuss sex between adults and children and criticise bourgeois society, particularly the power of mothers over their children. They are ''Récidive'', ''Interdit de séjour'', ''Portrait d'homme-couteau'', ''Le voyageur'', ''Paysage de fantaisie'', ''Journal d'un innocent'', ''L’Île Atlantique'' and ''Un anneau d'argent à l'oreille''. ''Paysage de fantaisie'', a sort of fever-dream set around a brothel in which the prostitutes are small boys, received the prix Médicis, thanks largely to the praise of literary theorist and homosexual Roland Barthes.
* ''Kim, min elskede'' (''Kim, my Beloved''), a Danish novel by Jens Eisenhardt. A troubled 28-year-old teacher and one of his male pupils, aged 14, fall in love with each other. The relationship continues into the boy's adulthood. There's also a sequel.
* ''Le visiteur de hasard'' (''Chance Visitor'') by Patrick Drevet. A high school teacher, hitherto heterosexual, married, loving father to a son, becomes passionately obsessed with one of his students, a not particularly remarkable lad of seventeen or eighteen. In the end [[spoiler:they have sex.]]
* In ''Golden States'', Michael Cunningham's first novel, a 12-year-old boy gets his first kiss from a young man in San Francisco.
* Gary Shelhardt's ''Kite Music''. A young American postgraduate student of teaching goes to Thailand on a teacher-exchange programme. There, he agrees to allow two 12-13-year-old boys to live with him since this will permit them to attend school. The teacher and one of the boys fall in love with each other and have an [[TeacherStudentRomance affair]]. The boy initiates the sex, climbing into bed with his teacher one night. Their relationship survives intimidation from American officials and blackmail threats. Eventually the boy becomes a monk.
* In Creator/StephenFry's ''The Liar'', the main character writes a play with a Victorian setting, in which a man rescues a 14-year-old boy from prostitution but then, to his horror, kind of accidentally sleeps with him. Said main character is in love with a slightly younger boy at his [[OneGenderSchool boys' school]] and also spends a while [[spoiler:...or does he?]] as a prostitute working Piccadilly Circus, picked up by older men. He's in his later teens at this point; some of the other boy prostitutes are as young as 11.
* In ''Magic's Price'' of the ''Literature/HeraldsOfValdemar'' series, Vanyel's DoppelgangerReplacementLoveInterest, Stefan, is much younger than he is. Initially Vanyel plays the mentor role to the young bard, refusing even the slightest hint of sexual attraction, but eventually the [[MindlinkMates lifebond]] between the two becomes impossible to deny.

* Relationships between older and younger men crop up in Andrew Holleran's novels.
* ''Reasons of the Heart'', by Bron Nicholls. In Australia in the late 1960s, 25-year-old Fred and beautiful 11-year-old paperboy Jonathan meet, and over the next year, a relationship develops between them. Jonathan lives with Fred from age 12 to age 17, when he leaves to be an artist. Ten years later, Fred is not over Jonathan and lives alone, but then Jonathan, who is now widowed and has a son with Down's Syndrome, reappears in Fred's life.
* Joseph Geraci's novels. In ''Marrying Tom'', two boys aged 13 and 16 have a relationship. In ''The Deaf-Mute Boy'', Maurice Burke, a former Jesuit, is now an archaeology professor at Columbia University and has an adult boyfriend, who has AIDS. While working in Sousse, Tunisia, he becomes close to Nidhal, the 13-year-old deaf-mute boy of the title, and also becomes involved with the boy's family. In ''Loving Sander'', Will, an American art scholar in his early 30s who likes boys, takes up a fellowship in the Netherlands and there falls in love with the 10-year-old son of a couple he's friends with. Over the next almost two years, Will and Sander have a close relationship, and when Sander is 11 they start having sex. Sander's mother seems to have a fairly good idea of what's going on, but she doesn't interfere. Sander is an eager participant and even offers Will sex with his, Sander's, friend Michael. Will has an adult friend who also likes boys and is defiant about his preference, conducting a relationship of his own with a boy, and taking photographs of him. At the end of the book, Will has to choose between returning to the US and staying in the Netherlands. He and Sander have declared their love to one another, but Sander is almost 12, nearing puberty, and starting to want independence from Will; the relationship will soon be over.
* Fernando Vallejo's semiautobiographical ''La virgen de los sicarios'' (''Our Lady of the Assassins''), which was later made into a film, portrays the love between a 50-year-old writer and a 16-year-old hustler and hitman in Medellín, Colombia.

* Matthew Stadler's novels all concentrate on man-boy relationships. In ''Allan Stein'', a man has an affair with a 15-year-old boy. There are also ''Landscape: Memory'', ''The Dissolution of Nicholas Dee'' and ''The Sex Offender''.
* The ''Literature/{{Nightrunner}}'' series has Seregil in the mentor role and Alec as the student. Interestingly, it was the [[UnequalPairing inequality in this pairing]] that kept Seregil distant for some time. After two books worth of [[HoYay subtext]], they finally received an [[RelationshipUpgrade upgrade]]. In an inversion of the trope, it is Alec's increasing maturity and skills that bring them together.
* In Paul Russell's ''The Coming Storm'', a 25-year-old man, Tracy, takes up a teaching job at a swanky [[OneGenderSchool boys']] BoardingSchool. The headmaster of the school, a married man, has a history of friendships with favourite boys at the school. He is attracted to Tracy and strikes up a friendship with him too, teaching him about classical music. Meanwhile, Tracy begins an affair with a 15-year-old pupil at the school, Noah. Noah has been sent to this school because he had a crush on a teacher at his previous school, and he makes many advances to Tracy before Tracy finally gives in. We also find out that a friend of Tracy's went to the school when he was a boy and had an affair with the then-headmaster, Jack. Another boy, a friend of Noah's, is having an affair with a 40-year-old man, a doctor.

* ''Return to Innocence'', which the author later adapted into a movie. 13-year-old Tommy has been mistreated by his mother for years; among other things, she prostituted him and made pornographic videos of him to put on the internet. When this is discovered Tommy is sent to [[BoardingSchool a group home]] for [[OneGenderSchool mistreated boys]]. The head of staff there is Glen Erskine, a married father, and a respected expert on male adolescent sexuality. Tommy has a relationship, including sex, with his counselor, another middle-aged married man with kids. The relationship is discovered and shortly thereafter [[spoiler:the man dies in a car accident.]] Tommy, believing Erskine is responsible, lashes out at Erskine, falsely accusing him, and Erskine ends up on trial for sex with a minor.

* In ''At Swim, Two Boys'', the three main characters are a young man in his twenties with a liking for teenage boys ("half-girl faces on man-sized bodies") and two sixteen-year-old boys who fall in love with each other. The man, [=MacMurrough=], buys the sexual services of the poorer and more experienced sixteen-year-old, Doyler. He then gets to know Doyler's innocent boyfriend, Jim, while Doyler is away. The realisation of Jim's innocence and deep love for Doyler shakes shallow, promiscuous [=MacMurrough=] to the bone, and he falls in love with Jim and refrains from making advances to him, though Jim flirts sometimes. Instead, [=MacMurrough=] teaches Jim to swim so that Jim can keep a pact with Doyler, and encourages his relationship with Doyler in other ways. He does this even though it hurts him to see Jim with somebody else, so much that he decides to leave the country, though [[spoiler:war eventually intervenes.]]
* Allan Hollinghurst's novels, especially ''The Swimming Pool Library'' and ''The Spell'', are full of attraction, sex, and relationships between older and younger gay men.
* In Mark Behr's ''Embrace'', the 13-year-old protagonist has two simultaneous homosexual love affairs while at [[OneGenderSchool his choir]] BoardingSchool, based on the Drakensberg Boys' Choir School. One affair is with his best friend, a boy the same age, [[TeacherStudentRomance the other]] with his 30-something choirmaster.
* Anafiel Delaunay and Alcuin in ''[[Literature/KushielsLegacy Kushiel's Dart]]''. Alcuin has to do a bit of convincing to get Delaunay to notice him, as the older man did see himself in more of a parental role... although as he had already trained the boy to work as a prostitute, he couldn't exactly claim Alcuin was too young or too innocent.
* In Alexander Chee's ''Edinburgh'', a 12-year-old boy, Fee, joins the Pine State Boys' Choir as a first soprano. He falls in unrequited love with Peter, his best friend in the choir. Turns out that the choir director sexually mistreats the boys, going so far as to drug them in order to do so. He is eventually caught, but the emotional fallout for the boys is heavy, and Peter and another boy later kill themselves. When in his middle teens, Fee is hit on by an older man, and he thinks about "how I could kill him". He also has a summer job working as a research assistant to an older man, who is a mentor for him and never lays a finger on him. At the man's funeral, he sees grown men of varying ages and realises that the man has had a series of adolescent boys work for him. Fee has a lot of gay sex during college but keeps on falling in love with straight blond boys who remind him of Peter. At thirty, he is in a stable, {{happ|ilyMarried}}y relationship with a somewhat younger man, whom he's married in a commitment ceremony. He then meets a blond 17-year-old boy, hitherto straight, who, in a subversion of the Lover/Beloved trope, falls in love with Fee and pursues him. Fee is attracted to the boy and they eventually meet for clandestine sex.
* In Michael Lowenthal's ''Avoidance'', 28-year-old Jeremy works as assistant director of a boys' summer camp where there is a strong emphasis on men mentoring boys. Jeremy agonises over his sudden attraction to 14-year-old Max, one of his charges. Turns out that Jeremy's own former mentor Ruff and the camp director Charlie both have similar predilections, but unlike Jeremy have used the mentor role to coerce boys into sex. Things are complicated by Jeremy's recollection that when he was 14, he desired the 50-something Ruff. There's a backstory in which, a few years ago, Jeremy had a friendship with a 13-year-old boy to whom he seems to have been subconsciously attracted.
* ''In Tall Cotton'', by Charles G. Hulse. Tots, a boy growing up during the Depression, has sex with boys and girls his own age, and with men. His male cousin, a few years older, then reveals that he is in love with him.

* Played with in ''Uncle Sean'' by Ronald L. Donaghe. 14-year-old Will meets his beautiful Uncle Sean, whom he has not seen for the past eight years, and falls in love with him. Sean is gay and devastated because his boyfriend has been murdered by his own side in Vietnam. Sean becomes reciprocally drawn to Will but is alarmed by his own feelings and refrains from acting on them. He tells Will that it is very important to find the right person to love. In the sequel, ''Lance'', Will does find love, with a boy his own age. In the next and last book in the sequence, ''All Over Him'', Will, conducting a LongDistanceRelationship with Lance, lives with Sean while going to university.
* Played with in ''Literature/{{Havemercy}}''. Roy is older and definitely a mentor for Hal, but is reluctant about entering a relationship with him for precisely that reason. He doesn't want to take advantage, and in fact, it's Hal who ends up as the pursuer for much of the novel.
* The medieval Japanese ''chigo monogatari'' ("acolyte tales"), written by various authors between about 1300 and 1500, tell of relationships between Buddhist monks and their ''chigo'' (literally "child"), young boys retained as assistants and acolytes. Some of the most famous include the tragic romance [[http://www.metmuseum.org/toah/works-of-art/2002.459.1 ''A long tale for an autumn night'']], and the unabashedly pornographic "Chigo scroll", which may be Japan's oldest preserved piece of pornography.

* Literature/{{Swordspoint}} ''The Fall of the Kings'' centers on the relationship between 28-year-old university professor Basil St Cloud and 20-year-old nobleman and student Theron Campion. Basil is TheBear and Theron is a PrettyBoy. Avoids the {{Squick}} factor due to the characters' ages and the fact that it's not quite a conventional TeacherStudentRomance, as Theron isn't ''Basil's'' student, but the age difference and mentor relationship are there, not to mention the focus on Basil's intellect and Theron's beauty.
* ''Literature/DragonBones'' has the relationship between the rather old (he is mentioned to have grey hair) high king Jakoven and the thirty-year-old Garranon. It started when Garranon was fifteen. [[spoiler:It is later revealed that Garranon secretly detests Jakoven, who exploited Garranon's vulnerable position as a child whose parents had just been killed by Jakoven's soldiers. ]]

* In ''Literature/MagpieMurders'', successful crime author Alan Conway and his "boyfriend", a prostitute who is young enough to be his zon.
* In the Creator/DanielleSteel novel ''Dating Game'', Steel proves that her MayDecemberRomance fetish isn't limited to heterosexual couples when the GayBestFriend of the protagonist is shown to be in a happy relationship with a man 20-25 years his senior.
** It's also one of the subplots of ''Family Album'', where a young man is seduced by an older actor and they have a blissful relationship for several months.

* In ''ComicBook/TopTen'', DaChief Steve Traynor and his partner Wulf have been a couple for about 50 years, but the prequel graphic novel ''The 49ers'' revealed that their relationship started when Steve was still a teenager and Wulf was about eight years older. It attempts to avoid the more dubious elements of this trope by having Steve actively pursue Wulf, and Wulf at one point explicitly challenges Steve about whether he's emotionally mature enough for a relationship.

* In ''ComicBook/TheAuthority'', the Midnighter and Apollo are much the same chronological age, but the emotional contrast between the [[TheCowl cynical, jaded and violent]] Midnighter and the [[TheCape much more optimistic and joyful]] Apollo gives them a touch of this relationship dynamic.

* In ''FanFic/SithAcademy'', a parody of ''Franchise/StarWars'' with Darth Maul as the VillainProtagonist, this is pretty much standard for Jedi Masters and their Padawans, with Qui-Gon Jinn and Obi-Wan Kenobi's relationship being especially saccharine at times. A number of stories mention former male Padawans of Mace Windu, and even Yoda gets into the act with his students. It's hinted that {{Teacher Student Romance}}s are equally common for Jedi partnerships where both are female, or when one is male and the other female, but no couples of these sorts appear in the stories. Curiously, even though Sidious is homosexual and Maul is bisexual, it's explicitly mentioned that relationships are forbidden between a Sith Master and apprentice because they would either be too competitive with each other or else tend to mellow out and lose their edge. This doesn't stop either of them from having WarShip trysts with the Jedi, however.

* Gender-swapped in ''Film/MadchenInUniform'' (''Girls in Uniform'') (1931), based on Christa Winsloe's play ''Gestern and Heute'', which itself is based on her novel ''Das Kind Manuela'', in turn based on Winsloe's experiences at school. The school in the film is, like Winsloe's, a [[OneGenderSchool single-sex]] BoardingSchool for the daughters of the upper classes, and is run on very strict lines. The young Scripture teacher, Fräulein von Bernburg, is the only adult there who shows the girls any kindness or affection, and as a result, many of them fall for her. Sensitive, motherless Manuela von Meinhardis, fourteen and a half years old, falls particularly hard, and Fräulein von Bernburg seems to have feelings for Manuela in return, though, as she explains to Manuela, she can't play favorites. When Manuela accidentally gets drunk and proclaims her love in front of the entire school and the headmistress, the horrified headmistress comes down hard on her, and she [[spoiler:nearly kills herself. In the novel and the play, she does kill herself.]] The film was a big hit on the lesbian scene in Berlin, which at that point was quite active and open. The Nazis, irked less by the film's homosexual content than by its portrayal of the schoolgirls collectively rising up against authority, tried to destroy all copies of it, but fortunately failed. The United States government attempted to ban the film, but Eleanor Roosevelt persuaded them not to.
* ''Zéro de conduite'' (Film/ZeroForConduct), a 1933 film by Creator/JeanVigo, the story of a rebellion at a [[OneGenderSchool boys']] BoardingSchool. An older and a younger boy have a homoerotic friendship, while the science teacher seems keen on patting the head and hands of the long-haired, 'sissy' younger boy.
* In ''Film/Victim1961'', which uses elements of the plot of ''Different from the Others'', a lawyer nearing 40 gets to know a young man about half that, who hero-worships him and with whom he shares a mutual attraction, though the older guy breaks it off because "he was getting too fond of me" -- or, as his wife suggests, "you were getting too fond of him". Said young man has also had a relationship with a middle-aged bookshop owner, who is deeply in love with him and wants to give him a home and a job for life.
* Comes up in ''Film/{{If}}'' by Lindsay Anderson, set in a BoardingSchool [[OneGenderSchool for boys]] thirteen to eighteen, where it's common and accepted for older boys to take a shine to younger ones. One of the three main characters has a relationship with a younger boy, of whom he's protective, but who seems to be a more mature person than his lover.
* In John Schlesinger's ''Sunday, Bloody Sunday'' (1971), a doctor in his fifties is having an affair with a 25-year-old male artist, who's also having [[{{Polyamory}} an affair]] with a woman. Both partners are a bit [[GreenEyedMonster jealous]] over their younger lover. We also see another man in his 20s whom it's implied the doctor has had sex with before, perhaps [[TheOldestProfession paying him for it]]. Originally, the age difference wasn't intended to be so large: Schlesinger had wanted Alan Bates, then in his mid-thirties, for the part of the doctor, but Bates couldn't do it so Peter Finch, mid-fifties, played the role instead.

* ''Butley'' (1974), the film of Simon Gray's play about a professor of English whose wife and younger boyfriend each, on the same day, leave him for another man.
* ''Die Konsequenz'' (''The Consequence'') (1977): Martin, an actor of about 30, is sent to prison for sex with his 15-year-old boyfriend -- who now has a girlfriend. Martin meets Thomas, the 16-year-old gay son of the prison warder, and the two fall in love and, at Thomas' instigation, have sex. When Martin gets out of prison he finds that Thomas' parents and boss reject Thomas because of his homosexuality, so he and Thomas leave town together, get an apartment, and plan for Thomas to go back to school. However, Thomas is taken away by social services and sent to a very unpleasant home for delinquent boys. Martin breaks him out, but Thomas ends up with an older man who says he'll help him but instead blackmails him into becoming his boyfriend. Then the older man throws Thomas out and Thomas becomes a [[TheOldestProfession prostitute]] and finally, having nowhere else to go, returns to the boys' home. At 21 he is released and he and Martin, who in the meantime has had a casual boyfriend nearer his own age, reunite, but [[spoiler:Thomas seems irretrievably damaged. He attempts suicide and then runs away from hospital, and there the film ends.]]
* ''Du er ikke alene'' (''You Are Not Alone'') (1978): another tale about an older and a younger [[OneGenderSchool boy]] at BoardingSchool. The older boy, fifteen, is something of a teacher and protector for the younger, twelve, who looks up to him. As is common with this trope, the older boy is the more sexually interested: he catches sight of a pretty face and goes for it. The younger boy, who masturbates already but whose sexuality may not yet be very strong or defined, is happy to go along with things out of affection and admiration for his older friend.
* ''The Lost Boys'', a 1978 BBC miniseries by Andrew Birkin. It's a fictionalised account of J. M. Barrie's (''Literature/PeterPan'') relationships with the five Llewellyn Davies boys.
* Arguably, ''Une histoire sans importance'' (''A Story of No Importance'') (1980), which is about the homoerotic friendship between two teenage boys. Though there's only about a year's difference in their ages, they conform to most of the classic elements of this trope. Philippe, the elder, is gay and falls deeply in love with Claude, the younger. Claude, on the other hand, is basically straight and sees flirting with Philippe as a game. During an argument, Claude says, "I was a kid back then. You taught me things." Philippe is frustrated that Claude is not a deep thinker and they can't talk about ideas together. When they eventually have sex, it consists of Philippe masturbating Claude. [[spoiler:Eventually, Claude turns to girls, leaving Philippe broken-hearted.]] These are all things you can find in many lover/beloved tales with a wide age gap between the pair. At one point, Claude is eyed up on the street by a grown man. It's a brief moment but full of implication, given the ending of the film, in which [[spoiler:Claude has sex with Philippe [[TheOldestProfession for money]].]]
* In ''Film/VictorVictoria'' (1982), this trope is Victoria's cover story: she disguises herself as a young man in this sort of relationship with the older Toddy.
* Played with in Patrice Chereau's ''L'Homme blessé'' (''The Wounded Man'') (1983). Henri, an innocent lad in his late teens, is waiting to see his sister off at the railway station when he realises that he is being watched by another man. He follows the man to the men's toilets, where he finds him being assaulted by another man. The other man suddenly kisses Henri, whereupon Henri becomes obsessed with him. He returns to the station to find this strange older man and insists on following him about. The man, who is gay, is a jaded crook and pimp, but Henri falls in love with him and becomes a [[TheOldestProfession hustler]] in order to please him.
* In ''Abuse'' (1983) by Arthur Bressan, who spent most of his career making gay porn films, a 31-year-old gay film student is making a documentary about child abuse. He meets Thomas, a somewhat effeminate 14-year-old whose parents have brutally physically mistreated him for the past six years, and Thomas becomes the centrepiece of the documentary. Thomas is also gay and becomes interested in the filmmaker. They have a relationship, and eventually [[spoiler:run away together so that Thomas can escape from his awful parents.]]
* ''Il sapore del grano'' (''The Flavour of Corn'' / ''The Taste of Wheat'') (1986). Lorenzo, a university student doing a year's teaching in a rural area, develops a romantic friendship with twelve-year-old Duilio, one of the boys in his class. The lover/beloved dynamic is played with. Lorenzo brings Duilio an encyclopedia as a present; Duilio teaches Lorenzo to drive a tractor and identify trees and offers him the simple affection that Lorenzo, who lacks a family and whose (rather vigorous) sexual relationships with women are emotionally unsatisfying, needs. When Lorenzo's girlfriend, seeing a postcard from Duilio, asks if he's one of Lorenzo's pupils, Lorenzo says, "No, he's the one who taught me everything I know." Lorenzo is made uneasy by his sexual attraction to Duilio, particularly when Duilio's family, with whom he has also become friends, grow uneasy too -- the stepmother because she thinks, mistakenly, that Lorenzo has done something sexual with Duilio, the father because he sees that Duilio loves Lorenzo more than Duilio loves him, the father. Eventually, though the family decide they like Lorenzo again, [[spoiler:Lorenzo leaves the village, even though Duilio longs for him to stay.]]
* ''Now That It's Morning'' (1991). A 15-year-old schoolboy attends his boyfriend's 45th birthday party. The guests at the party, all gay men, make snide comments about the boy's youth and the man, drunk, loses his temper and gives them a piece of his mind.
* ''Voor een verloren soldaat'' (''For a Lost Soldier''), a 1992 film set during the Second World War, portrays the brief love affair between a twelve-year-old Dutch boy and a young Canadian soldier, with elements of this trope invoked. The sourcebook, an autobiographical novel by choreographer Rudi van Dantzig, portrays the soldier pretty much forcing himself on the boy, who is upset by this but is also drawn to the soldier and keeps coming back to him. The film turns this into a gentle, consensual romance.

* ''Smukke Dreng'' (''Pretty Boy''), a 1993 Danish film. A 13-year-old boy runs away from home and gets into robbery and [[TheOldestProfession hustling]]. He has a relationship with an astronomy professor, whom he's drawn to because he's also interested in astronomy, but the man also has an adult girlfriend and throws the boy out when she comes home from vacation. The boy is angry and wants revenge.
* ''Total Eclipse'' (1995), a fictionalised depiction of the love affair between poets Paul Verlaine and Arthur Rimbaud.
* ''Pianese Nunzio Quattordici Anni a Maggio'' (''Pianese Nunzio 14 in May'' / ''Sacred Silence'') (1996). A 28-year-old priest is struggling against the Mafia in his neighbourhood. He's also having a [[PedophilePriest relationship]] with a 13-year-old boy, who plays the organ in the church and serves at the altar. His enemies find out about the relationship and to bring the priest down force the boy to tell social services about it. As seems to be quite common with this trope, only the older boyfriend is gay; the boy, though he enjoys sex with the man, is basically heterosexual and is also having a relationship with a girl. As also seems to be common, the man has previously had a relationship with another boy, but turned to a younger model once the boy outgrew his interest.
* Surprisingly overt in 1940 Hollywood production ''Film/StrangeCargo'', about prisoners escaping from Devil's Island. Moll and Dufond are coded as gay lovers. The hardened, brutal Moll is surprisingly affectionate and gentle with the younger, fresh-faced, decidedly less masculine Dufond. Moll promises Dufond good times and excitement if they stick together after making their escape. And after Dufond dies of exposure and dehydration, Moll compares himself and Dufond to Verne and Julie (Verne being another escaped prisoner, Julie TheChanteuse who went with him), wondering if Julie will miss Verne like he misses Dufond.
* ''Wilde'' (1997), a fictionalised account of the relationship between Creator/OscarWilde and Bosie. Stephen Fry plays Wilde.

* ''F. est un salaud'' (''Fögi Is a Bastard'') (1998), based on a novel of the same name by Martin Frank, set during the 1970s. 16-year-old Beni is a big fan of 26-year-old rock star Fögi. They meet and start a relationship; Beni leaves home to be with Fögi and Fögi breaks off his relationship with a male band member his own age. Initially, the relationship is happy, but Fögi has a lot of emotional problems, particularly a terrible fear of ageing, and things [[DestructiveRomance go downhill]]: Fögi persuades Beni to have sex with older men [[TheOldestProfession for money]], Beni ends up being in [[TheTwink porn photos]] and a [[UsefulNotes/{{BDSM}} D/s]] element enters his and Fögi's relationship. Beni goes along with everything because he is very deeply in love with Fögi. Eventually [[spoiler:Fögi persuades a reluctant Beni to commit suicide with him. Fögi dies, Beni lives.]]
* ''Literature/LoveAndDeathOnLongIsland'' (1998), in which an out-of-touch professor falls hopelessly in love with a shallow male teen idol who represents his ideal of beauty.
* ''Film/GodsAndMonsters'' (1998), a fictionalised depiction of the last days of Creator/JamesWhale. Whale is famous both for directing ''Film/Frankenstein1931'' and ''Film/BrideOfFrankenstein'' and for being openly gay in 1950s Hollywood. The film portrays him becoming attracted to his new gardener, a handsome young ex-Marine. The gardener is straight but Whale assures him he has no sexual intentions. This turns out not to be the case, and the gardener freaks out.

* ''Krámpack'' (''Nico and Dani'') (2000). Two sixteen-year-old boys, friends since grade school, are vacationing by the sea. One, Dani, is falling in love with the other, Nico, but though Nico is well up for a spot of sex with Dani he can't reciprocate his friend's affections, since he [[IncompatibleOrientation only likes girls]]. Dani goes to a dinner party with Julian, a thirty-something gay writer, who knows Dani's father because Dani's father was his teacher at university. Dani wants to be a writer too, so he and Julian have something in common, and Julian is clearly attracted to him. Julian's friends are made uneasy by Dani's youth and try to warn Julian off -- his straight female friend, who gives Dani private English lessons, reminds Julian that Dani is a minor and that she could report Julian or talk to Dani's father. However, Julian and Dani do end up alone together, and [[spoiler:Dani makes an advance to Julian, who, initially hesitant, agrees to have sex with him after Dani tells him it's not his first time -- but then Dani walks out and goes home.]]
* The 2000 TV film ''Juste une question d'amour'' (''Just a Question of Love''), which was very popular in France and instrumental in making people there more relaxed about homosexuality. A 23-year-old man doing a microbiology internship hits it off with the 30-year-old guy he's working for. The older guy is out and has little patience with the younger guy's hesitation in telling his parents about his homosexuality.
* ''Eban and Charley'' (2000). 29-year-old Eban meets Charley, just turned 15, and they fall in love. Somewhat subverted in that Charley initiates the sex. The filmmaker said this was based on a true story he knew of: a teenage boy, mature for his age, had an older boyfriend; the man's friends disapproved of the relationship because of the age gap and the man broke up with the boy, who was devastated. [[spoiler:In the film the lovers get a happy ending: they run away together.]]
* ''L.I.E.'' (2001) Big John, a 55-year-old ex-Marine, respected local figure, and pederast, lives with a 19-year-old boy and also buys the services of teenaged male [[TheOldestProfession prostitutes]]. He tries to use his regular, callous seduction moves on 15-year-old Howie, but instead finds himself falling in love with Howie and sublimates his sexual desires to be the father stand-in Howie desperately needs. Howie becomes aware of his power over John and flirts with him, eventually [[spoiler:making an advance which John, very unusually for him, turns down.]]
* ''Return to Innocence'' (2001), of which the screenplay was adapted by Gary M. Frazier from his novel of the same name. 13-year-old Tommy has been mistreated by his mother for years; among other things, she prostituted him and made pornographic videos of him to put on the internet. When this is discovered Tommy is sent to [[BoardingSchool a group home]] for [[OneGenderSchool mistreated boys]]. The head of staff there is Glen Erskine, a married father, and a respected expert on male adolescent sexuality. Tommy has a relationship, including sex, with his counselor, another middle-aged married man with kids. The relationship is discovered and shortly thereafter [[spoiler:the man dies in a car accident.]] Tommy, believing Erskine is responsible, lashes out at Erskine, falsely accusing him, and Erskine ends up on trial for sex with a minor.
* The 2004 film of ''Theatre/TheMerchantOfVenice'' deliberately emphasised the Lover/Beloved {{Subtext}} between middle-aged Antonio and young Bassanio.
* Played with in ''Ang Pagdadalaga ni Maximo Oliveros'' (''The Blossoming of Maximo Oliveros'') (2005). Maxi is an effeminate gay 12-year-old boy from a family of petty criminals in the slums of Manila. He falls in love with a young rookie policeman, Victor, when Victor rescues him from an assault. Maxi seeks out Victor's company and the two become friends, Victor advising Maxi to go to school, get a good job and stay away from crime. The other policemen tease Victor about being Maxi's boyfriend, but Victor turns down Maxi's romantic overtures, leaving Maxi heartbroken. At one point, however, Victor calls Maxi pretty and strokes his hair, which is probably just chaste affection but carries a possible hint of HoYay. At the end of the film [[spoiler:Victor waits to speak to Maxi but Maxi walks by him -- just possibly an UnrequitedLoveSwitcheroo.]] Filipino audiences may read the film quite differently to Western ones, however.

* ''The Mostly Unfabulous Social Life of Ethan Green'' (2005). The 26-year-old protagonist has a couple of relationships with guys his age but also one with a 19-year-old, who in a subversion [[spoiler:decides that his older lover is not mature enough for him!]]
* ''Tre somre'' (''Three Summers'') (2006), a Danish short film. A man in his 40s is going through a string of relationships with somewhat younger women. One summer, the 14-year-old son of a friend comes out as gay to him. The next summer, the boy, now 15, seduces him and they have drunken sex. The summer after that, they meet again and the man says that they can't sleep together again and must keep it quiet that they once did, but he agrees to give the boy a farewell kiss.
* ''Film/LittleMissSunshine'', a popular family comedy from 2006. Frank, a renowned Proust scholar (Proust was gay) fell in love with a male [[TeacherStudentRomance graduate student of his]]. This younger man left him -- for another older man, Frank's rival Proust scholar. Being upset, Frank acted up and got kicked out of his job. Then he couldn't pay the rent and got kicked out of his apartment. Then he found out that his rival in love and work had won an honour instead of him. So he [[DrivenToSuicide slit his wrists]]...but he survived. The film begins with him in hospital.
* In ''Avant que j'oublie'' (''Before I Forget''), a 2007 film about an aging gay man, lover/beloved relationships between older and younger men are the only kind portrayed. Often, the older man feels more attraction and affection for the younger one than vice versa, and the younger man is partly in it to have money left to him.

* The 2007 British TV film ''Clapham Junction'' subverts this trope. A 32-year-old man, suspected by locals of being on the sex offenders' register, lives in the neighbouring tower block to a 14-year-old boy. The boy sees the man through the window and is very attracted to him, in fact masturbates while watching him. The boy eventually goes to the man's flat and seduces him. The man is also very attracted to the boy but he's afraid of the consequences of having sex with him and takes a good bit of persuading. They have anal sex, and the boy 'tops'. When the boy's mother and father find him there, and his mother suspects what's happened and becomes furious, the boy staunchly denies it.
* ''James'' (2008). A boy of 15 or 16, [[OlderThanTheyLook looking younger than his age]], gay, friendless, and bullied, goes to a local public toilet where men meet for sex. A middle-aged man with a suit and a nice car approaches him in the toilet, promising "We won't do anything you don't want to do", but he leaves. On another day, [[spoiler:he comes back, sees the man outside the toilet, gets in his car, and says, "Do you know somewhere we could go?" The car starts, the film ends.]]
* ''En forelskelse'' (Awakening) (2008), a Danish short film. A 16-year-old boy meets his new girlfriend's parents and ends up having a brief, awkward secret [[LoveTriangle affair]] with the dad. Subverted in that the boy is the one who makes the first move.
* The German TV film ''Guter Junge'' is about a man who finds out that his 17-year-old son likes younger boys and doesn't know what on earth to do about it. Sven, the son, has a relationship with a fatherless, neglected boy of 12 or 13, Patrick, whom he tutors after school, and who plainly looks up to him. However, the trope is subverted in that with this boy and with an 11-year-old he's seen hanging out with at a party, Sven is happy to follow the boy's lead. Patrick wants to be an actor, so the two go to the movies together. The other boy wants to play the family CD collection for Sven, so that's what they do. Far from getting a kick out of being the 'older man', Sven is fixated on boyhood: he keeps his old toys around, shaves all his body hair, and feels glum about turning 18.
* עיניים פקוחות‎ (Eyes Wide Open), an Israeli film from 2009 about the forbidden, secret love affair between two Chassidic men in Jerusalem. Aaron is a married man, probably in his middle thirties, with four young sons. His father, a butcher, has recently died and Aaron takes over the butcher shop. He meets Ezri, in his early twenties, with nothing to do and nowhere to stay, and gives him a job and a room at the shop. Aaron teaches Ezri the butcher's trade, gives him advice, and 'tops' when they eventually do have anal sex. So far, so classic Lover/Beloved -- but it's Ezri who's more homosexually experienced, and who makes the first move. Ezri is shown to have had an earlier affair with a man nearer his own age.
* ''Film/CallMeByYourName'' (2017) along with the novel it's based on is a modern example, being about the relationship of 17-year-old Elio and 24-year-old American academic Oliver. Slightly subverted in that Elio is the one to more actively pursue the relationship, but in the end, Oliver, with a single intimate touch, is the one to initiate it.

* ''Series/TippingTheVelvet'': A number of the rich lesbians in Ms. Lethaby's circle have partners much younger than them who are kept women. Nan is Diana's Beloved ostensibly, though she's more essentially a sex slave.

* The latter half of season three of ''Series/{{Hannibal}}'' [[TheyDo reveals this as its endgame for Will and the titular psychopath]]. While Will is an adult in his early thirties, he's about a decade younger than Hannibal, highly vulnerable and susceptible to manipulation, and [[MrFanservice quite easy on the eyes]]; Hannibal in return is older, highly educated, appreciative of the Classics in art, music, and philosophy, and [[ImAHumanitarian has rather epicurean tastes]]. What starts out as an amusing side project to see how far Will can be pushed before he snaps becomes something else entirely as Lector becomes more and more obsessed with proving to Will that they are the same. Hannibal instructs Will on a wide variety of subjects and the two have a series-long, protracted debate about the ethics of murder, and artistic perception and appreciation of suffering as divine. [[InLoveWithYourCarnage Ultimately, Will capitulates, working with Hannibal to violently murder another serial killer and afterwards admitting that he thought of it as beautiful]], [[TakingYouWithMe before embracing Hannibal and throwing them both off a cliff and into the sea]]. Season three's Italian setting and continual references to Greco-Roman art, philosophy, and aesthetics cement the connection.