Yeah, if you believe "dude" is truly gender neutral, ask a straight male dude how many dudes he's slept with. Then you'll find out just how not neutral "dude" actually is.
LOL true. In reality I generally use they/their/s unless I know the preferred gendered pronoun the person uses. Never had an issue with it myself but can see how it can be confusing.
"How many y'all's slept with?"
"How many you's have you slept with?"
"How many they's have you slept wiht?"
I think any pronoun in this sentence sounds weird, so putting dude in it doesn't really prove much.
Well, yes, pronouns
are weird in that sentence. You couldn't ask "How many shes have you kissed" without the grammatical oddity calling attention, either.
"Dude," however, is generally a noun, & only extended to use as a pronoun in limited, colloquial circumstances, the same under which you'd see "bro," "man," or "girl" used as a pronoun - e.g. "Pull yourself together, man!" or "Girl, get out of here" operating in the same mode of direct address as "Dude, check out this car."
"Dude" as a countable noun is no more strange than other nouns in that query - its frequent distaff counterpart "chick," or on to "lady," "fella," "gal," "guy," "girl," "boy."
Whether dude is gendered or not, especially as a collective plural is regional & generational, if not even more specifically situational. My generation's media was filmed in (& idealized) southern California, so 'dudes' reads largely as gender-agnostic to me in the same way a mixed-gender collective in French is always "ils" - because personhood carries a notional default masculine gender in both those cultures. Once you raise the specificity of the context, however, such as by asking how many dudes a dude has slept with, that default masculinity can come to matter. (Or not, if they truly embrace dudehood as I learned it in my youth. Be excellent to each other.)
If you're not sure of reception with collective plural pronouns and don't have "y'all" or "yinz" in the local vernacular, it's pretty easy to substitute "Hi guys!" or "Hi dudes!" with "Hi everybody!"