“When’s your birthday? 23/10. When are we going to Mum’s? 19-29/11. When do you go back into therapy? 8/12.”

As it could be written in English in Britain, Australia etc.

23/10 is pronounced "23rd of October" or (usually) "23rd'f October" or "23rd'f the 10th".

The range is "19th to 29th of November" or "... of the 11th".

The pronunciation "second of the second twenty-twenty" is usually used when the listener is writing, typing or confirming the date in figures.

It doesn't "work better" than any other system, you're just more used to it.

i think this especially goes for the English system vs metric measurements (though confusingly the English do not use the Imperial system, officially at least) Our brains are much better wired for binary systems like bushels and pecks rather than the French derived decimal system which is only good for studious things (like science) where you have of many orders of magnitude to keep track of regularly. Much easier to communicate/grasp half than 5/10ths.

Similarly the Sexagesimal notation, in common use (clocks etc), points to an generalization that would have been much better than the French system, where we rely on primes for increasing places in the number. Eg 4321(primal) would be 4x5 + 3x3 + 2x2 +1x1 = 34(decimal). Historically we may be stuck with counting on our fingers and toes though, through eternity.

The more "logical" Metric system which is not an extension of the "practical" Imperial system is inevitably bastardized and Creoled in everyday usage. Eg one buys a "Pound Plus" of Chocolate from Trader Joe's (500 grams!). Why is the choice is not one (or fice) Hectogram(s) vs one Kilogram i do not know... except that Hectogram is so obtuse/abstruse i had to google it! Maybe someone in a Metric country can correct me, if they think i am wrong using words like abstruse. One inevitably finds doubling and halving in everyday commerce.

We would do a lot better to extend to tripling, quintupling etc, like the Babylonians did, than directly to the (insane, in my opinion :-) French 10x Metric system.

Not that i am an American chauvinist. Eg i think the American middle endianistic dating system is off the wall weird, and i go out of my way to circumvent it.