Ska is silly and makes me think of two things:
(1) 14-17-year-olds who either really just want to be friendly laid-back guys, so they let horn players into their band, or know someone who does this and think that band is cool for doing it. This demographic seems to fervently hope beyond hope that they are doing something that is meaningful. They might only just now be beginning to think that maybe drinking or smoking pot is OK, if their older siblings are managing to do it and still be cool (due to the previous point, their first time experimenting is invariably a huge deal and the only thing they talk about whenever they do it again, for at least a year). They're usually Christian, and simultaneously distance themselves from their faith in order to look cool for older kids, and remain adherents to their youth group in order to feel like they're making a difference for younger kids (this is usually the reason why they've taken so long to think about drugs or drinking, or sex for that matter ... most don't end up approaching these aspects of life until college).
(2) 18-25-year-olds who never outgrew the above portion of their life, and now get drunk/high all the time but still cling to the simplistic ideal of being a friendly, laid-back guy. In between their crises of faith after realizing that church didn't hold all the answers, and their crises of musical self-image after realizing that most of their friends didn't listen to ska anymore, as well as their consistant troubles with school and employment, they often have slightly-to-extremely inflated images of the drama of their own life. Rarely will they go to a party where less than 20% of the people are high school friends of theirs. For many this number is 50% or higher.
Since these are basically the two kinds of people I've met in my experience who have been associated with listening to ska, I find it a hard genre to respect fully.