Just saw this one today, wanted to share it. It was in the listing for an old movie on TCM called “I Wonder Who’s Kissing Her Now” (1947) starring June Haver and Mark Stevens. This was the description of the plot (emphasis mine):
“1890’s songwriter Joe Howard goes from selling organs in Weehawken to writing for Broadway”.
I do not remember what old movie it is, but I remember a scene in which a guy is flirting with a girl, and she looks at him coyly and says, “Are you making love to me?” So apparently “making love to” used to mean “flirting with”. (Of course, in some circles, the definition of “flirting” has probably changed sufficiently so that those two terms might still be not too discrepant…)
I remember seeing comedians in the 60s on shows like Carson talking about getting “stoned” at parties and such. But they were talking about getting drunk.
Probably Horsefeathers. Thelma Todd asks the question of Groucho Marx.
Pro tip: if she has to ask, you’re not doing it right. 
In an ep of the TV show “Amos ‘n’ Andy,” Kingfish says to Sapphire, “There’s men in the death house gayer than you!” (Sapphire was frequently unhappy with Kinfish’s shenanigans, and frequently called him on them.)
I’m not sure of this one; but it’s occured to me that people from before gunpower weapons probably wouldn’t understand the usage of “fired” ( or it’s ancestor word ) meaning “shot projectiles at”.
“What nonsense ! The Cupid of myth shot arrows at lovers ! He didn’t set fire to them !”
Yeah, it bugged me when Aragorn yelled “Fire!” to the archers at the Battle of Helm’s Deep in “The Two Towers” (the movie, of course; ol’ JRR wouldn’t have allowed such an anachronism).