A boy's boys' boys night out
A night out; for one boy; with his boys; typical of boys.
*puts on linguistic analysis hat*
It is that boy's night out.
(singular possessive)
That boy is having a night out.
It is the boys' night out.
(plural possessive)
Tonight belongs to the boys.
It is a boys night out.
A night out typical of boys.
I think I'm *more* confused now...