Total Recall.
Weirdly central to the novel and film Catch 22 was Nettly’s Whore.
I think Malcolm Reynolds and Inara Serra from Firefly also qualify, though it wasn’t the main focus of the series.
The protagonist of *Sexy Beast *married a porn star.
In the novel and film The Victors a featured portion is a where a major character falls in love with a woman who is a prostitute.
In film/Broadway musical South Pacific (or Tales of the South Pacific if you prefer the novel) doesn’t Bloody Mary pimp out her daughter to the lt.? And most definitely the Lt. falls in love with her.
In the film Cheyenne Social Club both the male leads (James Stewart and Henry Fonda) fall for prostitutes working at the “Social Club.”
In Action, the lead character has a relationship with a prostitute. I don’t think the character was in love with anyone but himself, but by Hollywood standards, it was a longstanding commitment.
In the original Battlestar Galactica, Starbuck had a relationship with a “socialator”. This was a 1970’s prime-time TV show, so they never explicitly called her a prostitute, but they dropped some pretty broad hints.
Nately. And darn you, I should have thought of that one. What was odd in this case was that the whore fell obsessively and homicidally in love with Nately only AFTER he’d gotten killed… at which point, she kept trying to kill Yossarian, whose only “crime” was being the one to give her the news of Nately’s death.
No, it’s just matchmaking; she wants Liat to marry the rich American.
The Owl and the Pussycat had a relationship between George Segal and part-time prostitute Barbra Streisand.
In The Mentalist, one of the team (Cho) falls for a hooker who is also a CI.
Blue World by Robert McCammon is about a priest that becomes infatuated with a porn star. Not exactly what you’re looking for, but it sounds close.
In Gone With the Wind, Rhett may not be in love with Belle Watling but he definitely loves her. He keeps up a relationship with her during his marriage and essentially moves in with her after his marriage collapses.
I would suggest going to some of the forums on prostitution and check out a few threads (you might need google translate, because these will typically be foreign boards).
If you need a few links, you can pm me… some chilling stories, with the added value of them being true.
Do they? IIRC, Jimmy Stewart does not even sample their wares (though Fonda does with some relish), and at the end they leave town with no romantic entanglements.
A real life case would be writer Stephen Crane. The love of his life was Lady Cora Stewart, 6 years his senior, who in spite of being the former wife of a baronet (who divorced her due to infidelity) was a madam in Jacksonville, Florida. Though they never legally married, they lived together until his death, he left her his entire estate (not much in and of itself, but the literary rights brought some income). After his death in a German sanitarium, she returned to Florida, opened a larger brothel, and married a signifincantly younger fourth husband before dying in her mid-40s.
It seems to be pretty common in Westerns.
In the movie Johnny Guitar it is strongly hinted that the Joan Crawford character is a former prostitute. The title character was in love with her.
On Dr. Quinn Medicine Woman, the telegraph operator Horace fell in love with and married a prostitute. Dr. Quinn’s adopted son also fell in love with a different prostitute but it didn’t last more than one or two episodes.
On Deadwood, definitely Sol Star and probably Al Swearengen are in love with Trixie. Jane at one point seemed to be falling for former prostitute Joanie.
On Gunsmoke, Miss Kitty may have been a prostitute and Matt seems to have been in love with her.
The Woody Allen film Mighty Aphrodite is sorta-kinda about this, but with lots of twists.
Pretty Woman.
Stagecoach. Can’t believe I forgot Stagecoach.
He also sets her up in business as a madame, and uses her whorehouse as a alibi after several of the town’s best citizens are accused of making a Ku Klux Klan raid.
Eva Duarte was a loose woman and might have been a prostitute. Juan Peron apparently fell in love with her.
Kinky!