I think this is very funny, especially for fans of Emma. It's a pretty good modern interpretation of that book: Cher (Alicia Silverstone) is privileged, popular, and well-intentioned, but she ends up causing various problems while trying to help others find love. Her lawer father is hilarious (to Cher's slick, smooth-spoken and cocky date, he says, "I have a .45 and a shovel. I doubt anyone would miss you").
Jon watched it with me. He hasn't said he hated it, and he laughed several times, so that's good. (I'm very grateful to have a husband who will watch chick flicks with me. And without making gagging noises or anything like that.)
One of the reasons Clueless works so well as a Jane Austen adaptation is that the high school is an excellent parallel to class in pre-industrialized England. In Austen's time, income, titles, and background meant everything; in high school, it's how you dress, talk and what you do for fun ("the loadies hang out on that grassy knoll"). Maybe it's easier to move between the "classes" in a high school, but I think the comparison works pretty well.