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Anime & Manga
- In Pretty Woman, wealthy businessman Edward Lewis hires Hooker with a Heart of Gold Vivian Ward to act as an escort for him for a week. Over that time he gradually falls in love with her, and she with him.
- In Chunhyang, the noble-born scholar Mongryong falls in love with Chunhyang, a cortesan's daughter.
- Deconstructed in Moulin Rouge!, where the courtesan unapologetically says that she's paid to "make men believe what they want to believe." Her seduction of a Duke who might have played this trope straight backfires nastily on both her and the penniless writer who genuinely loves her.
- Duke Leto's romance with Lady Jessica from Dune. She is not a prostitute or courtesan, but a member of The Order of Bene Gesserit, who ship off some of their younger initiates as concubines to powerful nobles in order to advance their genetic selection agenda. Despite this, Leto and Jessica genuinely fall in love with each other, and she even defies the order by giving birth to his son (initiates can choose the baby's sex at will, and she was supposed to bear a daughter).
- Judge Dee: It was entirely expected for a High-Class Call Girl to snag a rich husband this way in Imperial China.
- The judge once had to deal with the fallout of a high-ranking official committing suicide after being spurned by a courtesan, who was found dead soon after. The man's suicide had nothing to do with the courtesan, she just assumed he'd killed himself out of despair and used his death as publicity. In fact, he thought he'd caught leprosy like his father and killed himself before he became too disfigured, the father thought the girl was responsible and killed her out of grief.
- In another, he comes across a scam where a courtesan is to be bought off her madam by a high-ranking official despite already being freed. He recognizes the likely victim as his friend and colleague Magistrate Lo, and intervenes to prevent him adding the Gold Digger to his extensive harem.
- One short story has him accompany a young prostitute to her home, then listen to her problems, learning her fiance is about to be executed for the murder of a fellow officer's wife. When she tried to visit him in prison, she ended up flogged by the guards, badly scarring her chest (which is not good for her job, in addition to being a single mother). The judge saves the man's life, though he's not exactly grateful, telling the judge he has nothing to look forward to ever since his fiance quite sensibly never visited him in prison. The judge drops him off in front of his house, tells him his wife and son are inside, and leaves.
Live Action TV
- In Game of Thrones, Tyrion Lannister of House Lannister of Casterly Rock, one of the many noble houses in Westeros and by far the richest, falls in love with camp follower Shae, who becomes an Ascended Extra after Season 2.
- In Salem, Cotton Mather, a Puritan reverend, is in love with a prostitute named Gloriana, much to his father's dismay.
- Atherton Wing's infatuation with Inara Serra is this. Although he initially comes across as romantic, Atherton quickly reveals that he still very much sees the "courtship" as a transaction and stops acting nice when he realizes he can't buy Inara's exclusive attention.
- Inara's client during her introduction in the pilot made a similar offer (minus the coercion), and Inara and Kaylee later indicate that this happens fairly often.
- Inara and Mal's Belligerent Sexual Tension is an unusual example. Mal grew up the son of a wealthy rancher, but his home planet was glassed during the Unification War and he sank everything he had left into buying and fixing up Serenity before he and Inara ever met.
- In Man of La Mancha, the story within the story involves an older gentleman named Alonso Quijano falls in love with a prostitute named Aldonza. Because of his delusion, he believes her to be a lady he calls Dulcinea and refuses to accept that she is a prostitute.
- A quest in Mass Effect involves a Turian general feeling scorned at a high class courtesan's rejection of him and spreading false rumors about her.
- Empress Theodora of the Byzantine Empire began life as a sex worker (moving up from low-class brothel to stage performer and High-Class Call Girl). She eventually attracted the attentions of then-Prince Justinian and married him in 525 A.D., becoming a co-ruler of the empire with her husband and pushing through many reforms in women's rights, including an outright ban on forced prostitution.