It all depends on who I'm around. With my dad, I really didn't have to worry because I got a chunk of my musical taste from him so we're okay. My sister is the same way, but there's stuff I skip cause I know she hates it.
With my friends I don't really care, if they ask I'll skip it. If they don't have the balls to speak up, then I leave it alone.
The only two people I ever change my music for is my Grandma, who is an 89-year-old devout Christian woman and I'd like her not to die of a heart attack, and my boyfriend. Just because I know we have different taste. When we first started living together I would skip anything remotely "girly music" until he looked at my Music folder one day and told me he loved Jewel, reminded him of hanging out with his mom. So now the wall has come down there.
Sometimes I do the annoying blasting my music out of my car. Mostly if I had to have a really bad day and my car's radio makes this whining noise. Since I'm to cheap to replace it, I turn up my music to drown it out. One other time I get annoyed and do it, is when I pull up next to car blasting the Mexican Hat Dance stuff, cause where I used to live, that's all you'd ever hear. So I would start to play Flogging Molly, just to be annoying. It was fun for me.