"Yeah, but Monica, do you really want to be in a relationship where you can actually use the phrase, 'That's not how your dad used to do it'?"Love Father, Love Son is a love trope in which a person who can't have the person that they love for one reason or another winds up falling for their progeny (or descendant)—possibly because there's a strong resemblance in looks or personality, or maybe just because. The inversion is that the progeny develops an attraction to the person in unrequited love with their parent (or ancestor). Despite being primarily a love trope, this relationship may as easily be friendly or parental whilst retaining romantic undertones or a constant reminder of the unrequited love. In mundane settings, this is often preceded by Absence Makes the Heart Go Yonder and some manner of Time Skip (the person and their object of attraction were once romantically involved, were separated, then reunited years later) or Your Cheating Heart (the progeny's other parent was being cheated on). In fantastical settings, this is often a result of a Mayfly–December Romance, Human Popsicle or Time Travel. It may involve a Jail Bait Wait. See also Settle for Sibling, Wife Husbandry, and the Sub-Trope Squaring the Love Triangle. Compare My Grandson Myself, Identical Grandson and Generation Xerox. Contrast Parental Incest.
— Phoebe, Friends
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Anime & Manga
- In Mahou Sensei Negima!, Evangeline goes from Nagi to Negi.
- In Shimizu Reiko's A Million Pound Love, an 80-year-old millionaire asks a 20-year-old playboy to marry her. She is due to die in a few months and says that he will inherit all her money if he marries her. He agrees, but finds himself falling in love with her. On her deathbed, he discovers that it was not him she fell for, but his grandfather.
- Kare Kano (His and Her Circumstances), Asaba, a straight male, always had confusing feelings about male lead Arima. At the end of the series he hooks up with Arima's daughter.
- In Otome wa Boku ni Koishiteru, the protagonist discovers that his dorm is haunted by a Cute Ghost Girl. A little later, it is revealed that she is the ghost of his late mother's underclassman who was in love with her and is utterly smitten by her son.
- Implied in Neon Genesis Evangelion that Rei might have had feelings for Gendo at one point. When he turns out to not care for her at all, she starts to get attracted to Shinji instead.
- Extra squick points since Rei is a partial clone of Gendo's wife (Shinji's mother) and Lilith, which would make her Shinji's biological half-sister.
- Gendo had sex with both Naoko and her daughter Ritsuko, although he never actually loved either of them.
- Combined with Reincarnation Romance—in the messed-up, round-about way that only CLAMP can provide—in Cardcaptor Sakura: Yue was in love with Clow Reed. Clow dies, and Yue is sealed in a book. Later, Clow Reed is reincarnated as Fujitaka Kinomoto, and Yue's alternate form Yukito (and later Yue himself) falls in love with Fujitaka's son Touya. Follow that? (For added madness, Clow had intended for Yukito to fall in love with Fujitaka's daughter, the titular Sakura.)
- Also combined with Reincarnation Romance as well as Parental Incest in Umineko: When They Cry. After Beatrice Castiglioni dies, her lover Kinzo raises her daughter, convinces himself that her daughter is actually her reincarnated, and has a child with her once she is of age.
- In Kodomo no Jikan, this combined with Wife Husbandry and Kissing Cousins, is what Reiji's doing with Rin. He fell in love and was with her mother, but then she died of lung cancer. Now he's raising Rin to replace her.
- Fullmetal Alchemist gives us Big Bad Dante, who had planned to trick/seduce Ed into loving her—by taking over Rose's body, as a replacement for Dante's first love, Hohenheim.
- In Campione!, the ageless witch Lucretia Zola was in a relationship with Godou's grandfather back when he was young and handsome. In the present, she hits on Godou a lot, commenting that he and his grandfather are very similar.
- In Gankutsuou, Dantes and Albert (the son of Dantes' lover Mercedes and his backstabbing best friend) develop a friendly relationship with unrequited romantic undertones. Albert later proclaims that he loves Dantes and kisses him. In the original book these relationships did not exist.
- In Back Stage, the prequel novel to Love Stage!!, Rei is in love with Seiya, a married man, but ends up with Seiya's son, Shougo. In fact, Shougo is much closer to Rei's age and by the time of the main story they are happily commited.
- The Captain America example below is also in the comics: due to Comic-Book Time, Sharon "Agent 13" Carter was originally said to be the younger sister of Peggy Carter, but she's now her niece.
- An old EC Comics science fiction tale had an astronaut testing a faster than light spaceship. From his point of view, it works fine. Then he returns home and find that decades have passed. His girlfriend is now an old woman, married to his best friend. He ends up falling in love with their daughter, who is now his age.
- The Spider-Man: Sins Past storyline infamously reveals that Gwen Stacy slept with Norman Osborn, with whom she secretly had a pair of twins. Though Gwen was primarily Peter's Love Interest, she had dated Norman's son Harry as well.
- For added squick, Gwen's force-aged daughter then developed a bit of a crush on Peter Parker.
- Norman Osborn also had an affair with his son's new fiancee (the new Spider villain Menace). He's not a nice person.
Films — Live-Action
- Austin Powers in the first movie falls in love with and marries the daughter of his (married) female assistant from the 1960s, Mrs. Kensington.
- In the Captain America (1990), film after Cap woke up in contemporary times he fell in love with the daughter of the girl he was involved with in the 1940s.
- A gender-flipped version. In Bicentennial Man, the Android butler, Andrew, comes back after making himself more human and falls in love with the granddaughter of the woman he loved in the past, who looks exactly the same to the point that they are played by the same actress.
- In Hook, Peter Pan continues to visit Wendy as she ages. One day he returns to find her an old woman and is distressed that the girl he loved has grown old and forgotten how to fly. She tells him about her own granddaughter, Moira, who is asleep in her old bed. Peter promptly falls in love with Moira and decides to stay and grow up to be with her.
- In Drowning Mona Rona is playing wheel of fortune with both Jeff and Phil Dearly.
- This is gender-reversed in some adaptations of the French novel Le Bossu (The Hunchback), though not all of them. In the novel and its two major film adaptations, the hero marries his ward or adopted daughter, the natural daughter of his former love interest, who is herself the widow the man whose death he is avenging. In the 2003 French miniseries Lagardère, the titular character instead winds up with his original love interest after raising her daughter as his own.
- Ilsa, the extraordinarily fortunate villainess in Indiana Jones and the Last Crusade, gets to sleep with both Doctors Jones. Of course she's only using them but who says she didn't enjoy it?
Henry Jones: I'm as human as the next man.
Indiana: I was the next man.
- In Sharknado, there's at the very least a lot of Ship Tease between Nova and Matt, even though she had been infatuated with his father, Fin, up until meeting him. She's probably closer to Matt in age.
- Inverted in Space Truckers (i.e. Love Daughter, Love Mom). John Canyon, the aging trucker, has the hots for the waitress Cindy, who's agreed to marry him if he can take her to Earth to see her mother. As the story progresses, however, Cindy falls for John's new co-pilot Mike, and John decides to step out of the affair, since the youngsters are a better match for each other. In the end they reach Earth... where they meet Cindy's mom, who's been in cryostasis for years due to medical reasons, and as such is only slightly older than Cindy, and just as attractive. She and John immediately hit it off.
- In Casino Royale (1967), James Bond comes out of retirement, walks into his office, and bumps into Moneypenny. Exclaiming that she hasn't aged a day, he kisses her full on the mouth... only for her to reveal that she's actually Moneypenny's daughter. Bond looks appropriately abashed and keeps his hands off her for the rest of the film.
- A Song of Ice and Fire:
- Littlefinger, who was infatuated with Catelyn, seems to have this for her daughter Sansa.
- Inverted with the prostitute Shae, Tyrion's favourite, opportunistically shifting her affections to Tywin Lannister after Tyrion is tried for alleged regicide.
- Tower and the Hive series by Anne McCaffrey:
- Afra Lyon can't have the Rowan, so he marries her daughter Damia.
- Discussed in the book where Afra rejects this accusation by saying that he and Rowan were never meant for each other.
- Infamously in the Twilight series, when Jacob imprints on Bella's daughter while said daughter was still an infant. It's implied in his internal narration that he was only in love with Bella because she would be the mother of his true love, Renesmee.
- In The Judas Tree by Cronin. Somewhat subverted, though; the man is the one who ditched the first girl in order to marry a rich woman. Years later, he comes back and falls for his first love's daughter. It doesn't end well.
- A Love Triangle of this variety occurs during the Moirin trilogy where King Daniel marries Jehanne, who his son Thierry was in love with.
- In Pollyanna Grows Up, when Pollyanna and Jimmy discover that Mr. Pendleton was in love with Pollyanna's mother, they believe this is his intention, and Pollyanna feels obligated to marry him if he wants her. Fortunately for Jimmy, he doesn't.
- Deerskin, which is based off the fairy tale Donkeyskin, has the heroine's father becoming sexually attracted to her after her mother passes away from an illness.
- In Jodi Picoult's Second Glance, a man falls in love with a ghost and ends up with her granddaughter.
- In John C. Wright's Golden Age trilogy, Phaethon finds out his wife was trying to make good on a childhood crush on his father Helion, and was originally just trying to use Phaethon to get closer to him. By this time, they've been Happily Married for centuries, though, so it worked out.
- The Japanese novel Thousand Cranes plays this straight when the main character sleeps with his deceased father's ex-lover, then Gender Flips / inverts it when he falls for that woman's daughter, leading to a Did They or Didn't They? situation at the end. (For added fun, his father's other ex-lover is trying to set him up with another, unrelated woman while all this is going on.)
- In the Dénouement of Edgar Rice Burroughs's Warlord of Mars, Thuvia's hopeless crush on John Carter is showing every sign of being cured by meeting his son Carthoris. (Things go wrong so that she and he get their own book, Thuvia, Maid of Mars.)
- The Third Life of Grange Copeland is all over this: Grange was having an affair with Josie, and eventually runs off to the North. Then Josie starts sleeping with Grange's son Brownfield, who also sleeps with Josie's daughter Lorene. Then he marries Josie's niece, Meme, while Grange comes back and marries Josie. The whole family is already completely screwed up, and that's before Brownfield murders Meme.
- In Her Fearful Symmetry, Julia has a crush on the married Martin, which he declines. She later goes for his son.
- In Katherine Paterson's Of Nightingales That Weep, at the end of the novel, Takiko persuades her stepfather to marry her, arguing that he needs to marry, and a new wife would object to her as his stepdaughter.
- Several examples take place in the works of V. C. Andrews. Notably, Christopher of Flowers in the Attic is implied to have been in love with his own mother before transferring his affections to his sister Cathy; and Philip in the Cutler Series falls in love with Dawn and later becomes obsessed with her daughter Christie after Dawn dies suddenly in a fire. The most extreme example is Tony Tatterton in The Casteel Series, with four generations of women in the same family.
- A platonic example occurs in Harry Potter: Sirius was best friends with Harry's dad, which makes it difficult for him to relate to Harry normally.
- In Moon Over Soho, Peter's first clue that Simone isn't what she seems is when he takes her home to meet his mother, who immediately flies into a jealous rage, recognizing a former rival for her husband's affections.
- Judge Dee: One story features a general's son having an affair with one of the general's young concubines, even trying to murder his father and blame a local poet for it, the poet being known for trying to prove the general was a traitor and a coward. The general actually was guilty, having sacrificed part of his army in a secret deal with the enemy, but the murderer was someone else entirely, with nobler motives. The judge outright tells the son to commit suicide, as both the (attempted) patricide and the affair (considered incestuous) is a no-no in T'ang Chinese morality.
- An odd, Downplayed variation occurs in Warrior Cats. Cinderpelt develops feelings for Firestar, who is completely unaware of this and only likes her as a friend. Since Cinderpelt knows she has no chance with him, she encourages him to get together with Sandstorm instead. Cinderpelt's reincarnation, Cinderheart, gets together with Lionblaze, who is Firestar's grandson. Neither is aware (initially) that Cinderpelt and Cinderheart are one and the same.
- In Arrested Development, Kitty towards Gob.
- In the French TV series L'amour en héritage, the french painter was in love with Maggie (he was already older than she was), and then she left. He married some other girl, but then he met Maggie's daughter and had an illegitimate child with her. She died and he was left taking care of his daughter.
- The 4400 had Lily and Richard. When Richard was abducted, he was engaged to a woman named Lily. He was returned many years after her death, only to meet fellow abductee Lily—the original's granddaughter. The two fall in love and marry.
- In Friends, Monica is initially attracted to ex-boyfriend Richard's son, Tom. However, their first kiss ends up reminding her too much of Richard and she finds it creepy. Tom is forced to admit that she's reminding him too much of his mother and is equally freaked out. Needless to say, the relationship doesn't progress very far before it breaks down.
- On Angel, Cordelia went through seasons of Will They or Won't They? with Angel, only for Angel's suddenly grown son Connor to take an interest in her too. They wind up having a one-night stand, and Cordelia gets pregnant. Played with because Cordelia is secretly possessed by the season's Big Bad, Jasmine, when they had sex, and made creepier because her pregnancy is basically just to give Jasmine a new body, making this Parental Incest, sort-of-maybe, because Jasmine-in-Cordelia slept with Connor in order to make him Jasmine's father.
- In Robin Hood, an enemy of Sir Edward's wanted to marry Marian because of her resemblance to her mother, who had rejected him in favour of marrying Edward.
- Erica Kane from All My Children. She was married to Phillip Brent but it didn't last because he was still in love with Tara, the mother of his son Charlie. She then took up with Nick Davis, his biological father. Years later, she was briefly involved with Charlie Brent.
- In Once Upon a Time, Captain Hook develops a (largely) parental attachment to Baelfire, the child of his dead lover Milah by her husband Rumpelstiltskin. He later falls in love with Baelfire's former lover Emma Swan (who had a child with Baelfire). Yes, it's that kind of series.
- Oregon in Fresh Meat breaks up with her middle-aged professor and starts dating a guy her own age, who turns out to be her professor's son. She tries to avoid revealing to him that she screwed his dad.
- The Outer Limits (1995): In "Last Supper", the immortal Laura/Jade falls in love with the soldier who saved her from government experiments, and 20 years later his then-adult son because he reminded her of his father. He eventually supports their relationship.
- Though she didn't know it at the time, Night and Day's Jane Harper with Alex Wells and Josh Alexander.
- Inverted in Quantico. In the Flashbacks, Shelby and Caleb have a Friends with Benefits relationship. In the present, Shelby and Clayton, Caleb's father, are having an affair.
- On Star Trek: Deep Space Nine, Dukat is well-established as a Stalker With a Crush on Kira, but it takes a creepier turn when it's revealed that he kept Kira's mother as a concubine.
- In one episode of Roseanne, it comes out that David had an Erotic Dream about Roseanne. Dan doesn't think this is a big deal, and even admits—very reluctantly—that as a teenager he once had a similar dream about Roseanne's mother, Bev. (David, for the record, is mostly freaked out because this is after he's started considering Roseanne a Parental Substitute.)
- Game of Thrones:
- Littlefinger plants a kiss on Sansa after her mother Catelyn, his original crush, had died. She gradually wises up to his advances (especially after he has her married off to Ramsay) and has no intention of further humoring him once she comes into a position of power herself. Additionally, her brother Jon Snow outright threatens to kill him if he gets any funny ideas.
- Shae, a prostitute Tyrion falls in love with but sends away for her own safety, eventually betrays him and frames him for the murder of King Joffrey before he later finds her in his father Tywin's bed. Portrayed a bit differently than in the books since the whole Tyrion-Shae relationship is played up as a romance for the ages as opposed to Tyrion looking for love in the wrong place, with Shae becoming more of a Woman Scorned in this situation than someone driven purely by greed.
Myths & Religion
- The Bible:
- Joseph manages to barely resist an affair with Potiphar's wife. He later marries the daughter of a man named Potipherah, which is similar enough to Potiphar that some believe them to be the same person. (Averted in the Muslim version of this story, where Potiphar's wife is more sympathetic and eventually marries Joseph herself.)
- One Jewish tradition holds that Potiphar's wife wanted to sleep with Joseph because she knew from divination that they were destined to have descendants together—misunderstanding that those descendants would be through her daughter.
- Joseph's brother, Judah, inverts this trope: in accordance with the law of levirate marriage he winds up marrying Tamar, the widow of his two older sons.
- Leviticus forbids this kind of relationship, though apparently levirate marriage is an exception. The apostle Paul condemns this, to quote 1st Corinthians 5:1-2 NIV "It is actually reported that there is sexual immorality among you, and of a kind that does not occur even among pagans: A man has his father's wife. (2) And you are proud! Shouldn't you rather have been filled with grief and have put out of your fellowship the man who did this?"
- Greek Mythology:
- An odd example: in the Telegony, Odysseus had a son with Circe, Telegonus, who accidentally kills him. Telegonus then winds up marrying Odysseus' widow, Penelope, while Odysseus and Penelope's son, Telemachus, marries Circe, leading to a Tangled Family Tree.
- Another legend says that Telemachus marries Nausicaa, a princess who at least had some Ship Tease with Odysseus.
- On at least two seperate occasions, Zeus seduced women and men that were descendents from people he had sex with (Perseus was the great-grandfather of Herakles, for instance).
- Mordred, the bastard son (and nephew) of King Arthur, becomes obsessed with Arthur's queen Guinevere and winds up marrying her while Arthur's away. In the accounts where this was a consensual arrangement, Guinevere is this trope (though there are plenty of accounts where it isn't).
- Agatha Christie's play Go Back For Murder (based on her novel Five Little Pigs) is about a young woman, Carla, who upon coming of age re-opens the investigation on the murder of her father 16 years ago, which was pinned down on her mother Carolina (who has died in prison). The solicitor she goes for help remembers the trial and having a youthful crush on Carolina; by the end of the play, he and Carla get together. (This plot element was not present in the original book, where Carla goes to Poirot instead of the solicitor—as she used to do, Christie wrote Poirot out of the play adaptation.)
- Judge Turpin from Sweeney Todd: The Demon Barber of Fleet Street started the entire plot by having Benjamin Barker transported for life because he wanted his wife Lucy for himself. After having his way with her and driving her to poison herself, he adopts the Barkers' one-year-old daughter Johanna as his own. Fast forward fifteen years later, where Turpin finds out that Johanna has become every bit as beautiful as her mother was and starts lusting after her as well, to the point where he wants to marry her. Yes, this is every bit as creepy as it sounds.
- In Avalon Code, Mayor Georg married the granddaughter of his first love.
- In Devil May Cry 3, Dante encounters Nevan the Lightning Witch, a devilishly curious woman whose words sounds like she's a prostitute willingly offering to get into Dante's pants (she's either a succubus or leanashe; the game doesn't clarify). Her dialogue ("Your father was a handsome devil. But you're no slouch yourself") implies that she also had lusted after Dante's father Sparda in the past. Of course, the fans got a bit carried away with all of the Foe Yay/Ship Tease and as a result, Dante/Nevan enjoys a good deal of popularity among Dante's naval fleet.
- In Agarest Senki, Ellis is twelve when Leonhardt rescues her from certain death, and doesn't get a chance to grow up before he makes his Heroic Sacrifice. Being a long-lived High Elf, she settles for his near-identical Great Great Grandson Rex.
- Bizarrely inverted in the second Shadow Hearts game. Karin is in love with Yuri, but he can never return her feelings because he loves Alice. The good ending sends Karin back in time, where she meets and falls in love with Yuri's dad... Making her Yuri's mother.
- The Legend of Dragoon apparently tries to bridge this with a Love Dodecahedron, since Rose, who was involved with Zieg ten thousand years ago begins to fall for Dart, his son and is honest with herself about why. Things only get more complicated when Dart becomes involved with someone else and it's revealed that Zieg is still alive (and was happily married for at least a little while).
- A rare gay male version in Artdecade's sci-fi comic Threshold, in which a gigolo had sexual affairs with a corrupt executive and later his son after he died. Justified because in at least the latter instance he was a spy.
- In Girl Genius, Lucrezia Mongfish does this repeatedly, although in her case it's much more related to lust than to love. She at first mistakes the son of one of her former suitors for his father and later plans to seduce him, and is perfectly happy to flirt with the son of her other former partner. All the more complicated for the fact that she's inhabiting her daughter Agatha's body and both the sons have an intense Will They or Won't They? situation with Agatha.
- A Scotsman in Egypt has the mistress of Prince Charmless Adam take on a much more capable lover, taking up with the latter's son Robert after his father's death and her fall from grace (Adam taking actual interest in his wife once she gave him a son combined with the courtesan's fading looks). She makes the mistake of trying to blackmail Robert into killing the heir and raping the prince's wife by threatening to publish evidence that Robert's father and Adam were part of a plot to kill the current king back in their youth... and is murdered by a panicking Robert maybe two minutes after she tells him this.
- The Simpsons:
- Mr. Burns' illegitimate son was the result of a One Night Stand with the daughter of his old college crush.
Burns flashes back to the outdoors of the 25th Yale reunion feast of his Class of 1914. A much younger C.M. Burns sees his unrequited love of his college years, Mimsy Bancroft, a middle-aged woman staring back at Young Burns. Young Burns becomes wide-eyed as the narration goes on. "Of course, by then, Mimsy had her share of wrinkles and a grey hair or two, but my adoring eye saw past those minor imperfections—to her 21-year-old daughter, Lily."
- In one relatively early episode, Abe had a brief relationship with Marge's mother. Many seasons later he briefly married Marge's sister Selma.
- Mr. Burns' illegitimate son was the result of a One Night Stand with the daughter of his old college crush.
- In one episode of The Pirates of Dark Water, and elderly alchemist reveals that she was Ren's father's ex-girlfriend. She never got over losing Primus to Ren's mother. She later used a potion to restore her youth and blackmailed Ren into marrying her in a crazed attempt to reclaim her past happiness. Sadly, the potion backfired on her—likely because she used a drop of Dark Water to make it—and she suffered Rapid Aging. When Ren tries to apologize for his father jilting her, she absolves him and his father of blame saying that she was the one who couldn't let go of the past.
- Futurama has an Inversion—a night of Pity Sex turned Zapp Brannigan into Leela's Abhorrent Admirer, but a later episode has him go after her mother, Munda, instead. He actually did seem to care about her, but Munda eventually broke it off after seeing what a Manipulative Bastard he could be to other people.
- Also played straight when Fry is taken into the far future in a time machine that only goes forward (but is assumed by Leela to have died at a spring break party). Leela marries his nephew's clone when he has grown old enough to resemble him physically, they have a divorce that causes her to lose the company she was running.
- In Gargoyles, Goliath used to have a relationship with Demona, who later begins one with Goliath's clone/"son", Thailog. Who later tries to replace Demona with Delilah, who was created with a mix of DNA from Demona and Goliath's other Love Interest, Elisa.
- On Adventure Time, Tree Trunks invites her first husband to her wedding to Mr. Pig (her fourth husband). The ex winds up making out with Tree Trunks' mother.
- Family Guy:
- Peter is worried one of Lois' ex-boyfriends is trying to steal her from him. At the end of the episode he confesses to having sex with their daughter, Meg, instead. (Peter doesn't care.)
- Brian has long had a thing for Lois and once made out with Meg, though he regretted it pretty much immediately. (And Quagmire, of course, has come on to both of them.)
- In one episode Lois has a fling with Bill Clinton and, to make it up to Peter, offers to let him sleep with any woman he wants. To her utter amazement, he picks her mother. Though the mother is willing, they don't wind up going through with it.
- In another episode, Peter meets a hundred or so children whom he's fathered through sperm donation; one of them, Larry, is basically a less crude version of Peter and develops a mutual attraction with Lois.
- The Cleveland Show:
- Inverted in one episode, Junior and Donna (a stepson and stepmother) are in a ballroom dancing contest together and he becomes convinced the two of them are in love. Eventually he realizes that, having never been close to his own mother, he was just confused by their growing parent/child feelings. Though to top it off, the episode ends with the implication that he may have a thing for Roberta (Donna's daughter/his stepsister).
- One episode implies that Donna almost ran off with Cleveland's father Freight Train.
- In the last episode of the series, Donna's mother Dee Dee hooks Robert, Donna's ex-husband and the father of Rallo and Roberta. Most of the family is understandably unhappy about this.
- In yet another episode, Rallo has a Precocious Crush on Junior's Girl of the Week. Eventually they learn that she's a teenage mom, and Rallo instantly falls for her daughter instead.
- In American Dad!, Hayley begins dating Stan's CIA body double (yes, the Oedipalness is Lampshaded and actually used for a character arc). Said double eventually tries to pull a Bed Trick on Francine, but Stan comes home before anything can happen.
- Invoked in a Daria tie-in book, where Daria has to write a story for English class, and our orphaned protagonist goes to meet a mysterious nobleman: "Rumor has it that my mother (whom I resemble to an astonishing degree) had spurned his affections years before. But what was his interest in me?" Of course, since Daria is writing this, the protagonist quickly realizes that the nobleman is a vampire, kills him and loots the corpse.
- Irish poet W.B. Yeats proposed to Maud Gonne multiple times before proposing to her illegitimate daughter Iseult, who also turned him down.
- Mary Tudor was originally betrothed to her cousin, Holy Emperor Charles V, when he was 22 and she was 6. Perhaps understandably, he married someone else instead. Mary wound up marrying his son, Phillip, who was 11 years younger than her.
- German poet and writer Johann Wolfgang von Goethe proposed to his old love's very young daughter Ulrike. She didn't accept his proposal.
- Young Wu Zetian was a concubine to Emperor Taizong who was around 30 years older than her as she was 13 or 14 years old. After Taizong's death, his son Li Zhi was made emperor and made Wu his concubine. Both of them were approximately around the same age (Li Zhi was 21 when he call the 25 years old Wu back to the palace to be his concubine). It was speculate that Wu and Li Zhi have an affair while Wu was Taizong's concubine, as this would explain why Li Zhi decided to bring Wu back to the palace when she was put to a Buddhist nunnery after Taizong's death.
- Judith of Flanders married her first husband King Æthelwulf of Wessex when she was about 14 and he was in his mid-50's. When he died, she married her stepson Æthelbald who died 2 years later. Then her father told her to Get Thee to a Nunnery, but she later eloped with Baldwin I of Flanders. Baldwin's son Baldwin II married Ælfthryth, daughter of Alfred the Great, who was Judith's first husband Æthelwulf's son by his first wife Osburh (Alfred the Great and Æthelbald were brothers), which means that Ælfthryth was the daughter of Baldwin II's stepbrother through his mother's first marriage, so his stepsister once-removed.
- Germaine of Foix is a rare exaggerated example. She was married to Ferdinand II of Aragon, the king of Aragon, as his second wife, with around 30 years age gap between them. After Ferdinand's death, the 29 years old Germaine later on had an affair with his grandson, the aforementioned Holy Emperor Charles V, who was then 17.
- Stratonice, the Queen of the Seleucid Empire, was married to King Seleucus I of Nicator. They remained married for quite some time until one day, the prince Antiochus I of Soter, Seleucus' son by his first wife, received an unknown illness and was said to stave himself. Agonizing on his sickbed, nobody knows why or what caused Antiochus' sickness until Seleucus called for a Greek physician, Erasistratus, to check on his condition. Erasistratus realized Antiochus is suffering from lovesickness, his unrequited love for his own stepmother Stratonice as evident when Erasistratus noticed Antiochus's heart pulse quicken when Stratonice walked into the room. Erasistratus suggested to Seleucus that he should forfeit Stratonice and the kingdom to Antiochus in order to make his condition better in addition as he is the successor. Seleucus agreed and Stratonice married Antiochus; by most accounts they appeared to have a happy marriage.