Josh and Cher's relationship is predictable and, if you don't look too closely at it, adorable. But if you really look at how things progress between them, it's a little predatory. Josh is older than Cher by at least three years (a huge difference when you're talking about teens), and possibly more than that, as a college student. There are moments in Clueless when he gazes at her or flirts with her and, if they were both the same age, it might be a little more acceptable. But the truth is, Josh is an older guy and even before he and Cher have their long-awaited kiss, he is interested in her: a high school junior. It's a little icky.
When Josh and Cher finally realize how they feel about each other, he lists all of the things he admires about her. Spoiler alert — there are just three things and two of them are "beautiful" and "gorgeous." Oh yeah, and the other is "popular." Maybe Josh could have also said he admires how Cher takes care of other people and tries to be a good person. I get that Paul Rudd only had so much dialogue to work with, but his character would have been so much more of an adequate match for Cher if he actually said he saw beyond what everyone sees on the outside.
Maybe that kiss is supposed to just symbolize everything he feels?
