I'd say, the stereotype for a teenage boy includes: popular action movies; video games; adventurous books intended for teens; T-shirts with skulls or ironic sayings or soda logos on them; iTunes gift cards; cases of Mountain Dew or Red Bull.
If the giver has to rely on a list of stereotypes for ideas, then by your own standards, doesn't that mean the giver doesn't know the recipient well enough to know what the recipient wants?
This. I'm trying and failing to understand your logic, TootsNYC.
The point (my son's point, really, which I understand) is that it's not whether you succeed with the gift.
It's whether you point-blank acknowledge that you aren't willing to put any time or energy into thinking about what the person might like.
As MariaE so clearly delineated: Unwillingness, not inability.
If you gave my son his fifth copy of MarioKart, or MarioKart for a game system he didn't own (has happened) he'd be touched. He'd just take it to GameStop and trade it in. (heck, a relative of his just game him a green T-shirt bcs his fave color is green--he was happy!) But his feelings are hurt if the subtext of your question is, "I don't want to spend time thinking about what you might like."
So I think someone could ask him for ideas in a *way* that didn't have that subtext, and thereby avoid hurting his feelings.