There was an ongoing storyline in The John Larroquette Show about the relationship between Larroquette’s character and the prostitute character played by Gigi Rice.
But good luck on seeing this. NBC never released the series on any format for home viewing and it hasn’t been shown in syndication since 2005.
She wasn’t a prostitute, she was an elevator operator. In fact, when her proto-Mad Man married boyfriend (Fred MacMurray, awesome) gives her a hundred bucks in lieu of a Christmas gift, only then does she taunt him as though he sees her as a prostitute.
And since it was 1960, $100 meant high-class goods.
She was a doll, but like all such characters she got a lot “softer” as the series progressed. They finally ended up sleeping together in about the third season; it was memorable because David Crosby’s character’s ghost was there.
I took away one thing from that show: the sign on the back of John’s office, from an old-style carnival: THIS IS A DARK RIDE.
Prewitt fell for Lorene in From Here to Eternity.. The New Congress Club wasn’t as blatantly a brothel in the movie as in the book, but it wasn’t a secret.
It was a theme for a few episodes in The West Wing. Sam falls for a law student, not realizing she was financing law school by being an escort.
Ernest Borgnine’s cop and Stella Steven’s hooker were on their honeymoon in the original Poseidon Adventure.
There are a few examples in here: http://tvtropes.org/pmwiki/pmwiki.php/Main/HookerWithAHeartOfGold
L.A. Confidential, True Romance, Killing Zoe. (I feel like I could come up with these all day if I thought about it).
Arguably, Bob Dylan’s song, Simple Twist of Fate, is about a guy who falls in love with a prostitute (or, at the very least, a one night stand).
The 80’s were ripe with movies about madcaped adventures of being a pimp, only to fall in love.
The weirdest was “Doctor Detroit” with Dan Aykroyd. The strangeness of this movie needs be be seen to be believed.
Next is “Night Shift” with Henry Winkler and Michael Keaton and Shelley Long who pimp out of a mortuary. Still no where as weird as Doctor Detroit.
And finally “Risky Business” with a supposedly teenaged Tom Cruise and Rebecca De Mornay, which is barely weird at all.
Aykroyd actually did fall in love with Donna Dixon, one of the actresses playing a prostitute, during the production of this movie. They got married a few months later and will be celebrating their 30th anniversary this year.
I loved The Crimson Petal and the White and didn’t realize it had been made into a miniseries.
Notes From Underground, kind of, although the underground man was too messed up to really love anyone.
On the first season of The West Wing, White House Deputy Communications Director Sam Seaborn, played by Rob Lowe, has a relationship with a call girl, played by Lisa Edelstein (who’s only doing it to put herself through Law School).
Does this happen Crime and Punishment?
I can not believe I’m the first to mention Moulin Rouge!
Another opera, Kurt Weill’s and Bertolt Brecht’s Rise and Fall of the City of Mahagonny is centered on a brothel. It’s questionable how much love Jim has for Jenny, though.
Puccini’s Madama Butterfly counts if you’re cynical enough about Cio-Cio San.
*The Best Little Whorehouse in Texas *
The Australian TV series Rake features this theme and is highly recommended. (There will soon be an American remake starring Greg Kinnear, but I still suggest you watch the Aussie original.)
I feel like the character of “Mom” and her henchmen heavily influenced the character of Mom and her henchmen from Futurama.