What it means
A gentle little exclamation for when something's gone wrong but you're keeping it polite. It softens bad news or a small disaster without any fuss, the verbal equivalent of a sympathetic tut.
Usage examples
"Oh dear, looks like the train's cancelled again, best stick the kettle on and wait it out."
"Oh dear, you have put salt in the tea instead of sugar."
"Oh dear, the cat has knocked the whole plant off the sill again."
"Oh dear, I've sent that text to the family group instead of Jess."
"Oh dear, the cake's sunk in the middle, never mind, we'll still eat it."
Where it comes from
This one goes way back in English. It’s been around for centuries as a soft exclamation of pity, concern, or mild dismay, built from oh plus dear. The dear here isn’t about price, it’s the affectionate word, which gives the whole thing that gentle, cushioned little sigh of sympathy.