most of my friends just aren't bothered and stay in their safety zone

I know a guy very much into Opeth, Mars Volta, Dream Theater, but was nearly dozing off when I extolled the virtues of Canterbury prog - but those were their influences, godamit!

Exactly. There is nothing wrong with pushing someone in a new direction. If they don't like it then fair enough but why dilute yourself into something that you are not?

If you think that something is worth listening to then why not share it? it may usually come up with negative responses but if if you believe in it then what is wrong with being true to yourself instead of offering up music that you don't like in order to be accepted or admired?

Yeh, I don't care that much if people don't like music I like. I'm perfectly confident liking what I like, if someone doesn't like it I won't get butthurt. I'll argue the case for what I like of course because I like discussion and I can back up my opinion. But nobody can please everyone, it's impossible, so there is no point trying to. Judge by what you hear and can understand in you own mind.

I don't think that's the point. You already know what your friend likes so give them suggestions in the genres that they like what's wrong with that? it's not about being accepted or admired it's knowing what your friends already like and dislike.

It's good to have your tastes stretched though, I think it is anyway, to increase your understanding of music.

I agree but we are talking about getting a gift for a friend. Wouldn't you rather give them something you KNOW they will like rather than something that you think they may like but you aren't sure?

Well yeh of course, this conversation has kind of drifted off the specifity of that. Even then there is no absolute guarrantee they would like it I suppose. And perhaps people should just be happy getting a gift anyway.

not when a Beatles fan is getting an Emperor album

If you think a person isn't ready to hear album x (ie. they've never listened to free improv. or drone or avant-prog or shoegaze and therefore wouldn't know how to handle it), then you need to know enough about music to find what I call "bridge albums". If you want somebody to like album x, find an album that bridges what they listen to now with what you want them to hear. One of the best bridge albums I've come across is If You're Feeling Sinister by Belle and Sebastian, with its poppy nature and somewhat angular compositions, the more all-inclusive instrumentation, and whatnot... You can easily bend the rules. It's really not as hard as everyone thinks to get somebody to at least appreciate an obscure underrated genre.

Your gift can have some consideration for the other person if you take that route, but I still don't think it has to. I just do that because I'd rather they do have the 100% success rate of walking away with something they'll like. Doesn't mean I do that all the time, though.

I'm pretty sure a majority of us at music banter know what "bridge albums" are you didn't really need to explain it but I agree with your last paragraph though about having 100% success rate vs. say like 75% or something along those lines.