In an Archie comic book story from the 1960s, Archie has to hold Veronica's purse. Reggie see him, flashes a limp wrist, and says "Whoops, my dear!" Obviously he is implying that Archie is gay, but how?
In another comic strip, Mickey Mouse decides to put up flowered wallpaper. His friend then "accuses" him of being gay by dancing around and saying "Whoops, my dear!"
The phrase appears on The Carol Burnett Show (1970s), on the Burns and Allen radio program (1940s), in popular novels (1950s), in stand-up comedy routines (1960s). But what exactly does it mean, and how did it come to be an anti-gay slur?
The earliest use I have found is in a 1910 song by Bert F. Grant and Billy J. Morrisey:
Georgie was a dainty youth, well known for miles around.
Up on the street both night and day, he always could be found.
With his natty little cane and flaming crimson tie
When he'd come strolling down the lane, you'd loudly hear him cry, "Whoops, my dear."
H's a turn-of-the-century dandy, his cane and red tie symbolic of gayness, although in this song, he's courting women.
A Dictionary Criminal Slang (1913) lists it as a "jovial expression of fairies and theatrical characters"
Sounds like a mild expression of surprise.
"What Do We Care for Kaiser Bill", a World War I song (1917):
Now Percy left his home one day to join the flying corps
He said I'll make those horrid boys and girls feel very sore
The first time that they took him up, it made him feel so queer
When in the clouds they looped the loop, he yelled out "Whoops, my dear."
Percy (a gay-coded name of the era) yells out the phrase because he's feeling dizzy. He's probably been turned gay ("queer").
In the 1920s, tourists to Paris could go to the Petite Chaumiere at 2 Rue Berthe, where the "men dressed as women...cavort around and swish their skirts and sing in falsetto and shout 'Whoops, my dear."
"I Wish't I was in Peoria" (Billy Rose and Mort Dixon, 1925), tells us
They're yelling "Whoops my dear" in Peoria tonight.
They've got a big red-blooded warrior, he wears a red tie in Peoria,
Oh, how I wish't I was in Peoria tonight.
The song is about how the "hick town" of Peoria, Illinois is far more sophisticated than Manhattan. For instance, they have gay people there. Red ties still signified gay identity.
In 1932, the Green Street Theater in San Francisco was playing "the continental spicy musical cocktail Whoops, My Dear.", aka Die Guckloch (peephole). Mild expression of surprise at sexual shenanigans.
Whoops, my dear, even the chief of police is queer.
When the sailors come to town, lots of brown
Holy by Jesus, everybody's got pareses in Fairytown
A mild expression of surprise at the existence of gay people. I can't even guess what "lots of brown" means, but "pareses" is an inflammation of the brain that occurs in the late stages of syphillis.
(Shown: Gage Crosby, no relation, a University of Arizona swimmer).
Lucille Ball sang the phrase in "Hey, Look Me Over" in Wildcat (1960), about an attempt to strike oil in Texas (top photo: her costar, Keith Andes):
We're hitting the road
Loud as a Shanta Clare but jittery as hen
The road to glory running a "whoops my dear,"
but here we go again. Yeah!
We see here the final evolution of the phrase, from "I'm gay" to "I'm surprised that gay people exist" to "I'm surprised."