okay, so i have a weird time with this stuff.
i remember a year or so ago a friend of mine was finishing up his undergrad and was working on a group project at his house. i was over at the time, and someone said something to the effect of, "yo, what's up with all this gay-assesd weather?"
i mean, honestly, what does that mean? needless to say, it became a joke from then on in between myself and my friend. everything was "gay-assed" -- coffee, the news, socks, cell phones -- because it was so silly.
it's not hateful, but it is derogatory, and it makes you sound like a fucking fool to think that "gay" is a word that can be used in the pejorative.
however, i am fine with using "gay" to describe somethings. i'd call "Dreamgirls" gay, as well as "African-American." i'd call Drag Shows gay. i'd call many Westerns gay. i'd call nearly half the clothes in Banana Republic gay. gay is now a very clear cultural niche, and a straight person can wear gay, or see gay, or listen to gay, and not have it mean a thing about his sexuality.
so, to extend this, i would say that i did just buy a really gay pair of Pumas yesterday at DSW. wow, what a gay sentence. and i'm fine with that. because i'm acknowledging the stereotype/niche while i am fully aware that it's not all-encompassing, and that the non-gay can easily consume that which might be termed gay without much of a problem in the same way that i get tremendous (guilty) pleasure out of the new Beyonce single (which is also kind of gay).
so ... yes, if i were a middle school teacher and i heard someone using "gay" as interchangeable with "stupid" or, worse, "retarded," then i'd call him out on that. it's inappropriate, and it's less for the benefit of someone in the class who might have a gay uncle or lesbian mothers and more to make sure the kid doesn't walk around thinking that kid of language is acceptable and he makes an ass out of himself.
but it is slippery. when someone says "gay-assed shit," they don't mean gay as in homosexual, unless they're saying that "Moulin Rouge was a really gay-assed movie," which it kind of was, but then just how derogatory is that?
whatever. y'all can puzzle out this gay-assed shit yourselves.