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.
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