It really depends on the situation. If I'm drinking whisky with friends, I usually choose something the we all enjoy, and as most of my friends aren't really whisky drinkers, that would probably be a Highland whisky like a Balvenie, Dalwhinnie, etc. So I would stick to one, because not worth having a few bottles out for myself while only pouring one for guest(s) who don't really care that much what they are drinking.
If I'm drinking whisky with friends who are drinking other things, I might switch up, starting with something I really enjoy but as the night progresses, and I get a little tipsy, pull out whatever bottle I've been ignoring because it wasn't that interesting. At that point, the result of drinking becomes more important than the process.
More often than not, regardless of which scenario above, I probably switch to beer after a couple drams anyway - easier to control intake!
Alone, depends on the mood - some evenings are for sampling, some for savoring and really getting to know a malt.