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The first step in any haggling or auction circumstance is decide how much you want to pay. Never pay more than that.
Your opening offer should be the lowest number you think you can get away with. If you go too low, they'll ignore you as a crazy; take personal offense, if they have HBP or whatever; or just sell it to someone else.
50-33% of asking is a reasonable place to start, but if you know something about the item it's absolutely fine to offer much less. I.e.: they're asking retail price for a broken thing, and you want it for parts, it's fine to offer 5-10% of what they're asking.
If you think there's a substantial chance of someone else coming along and buying it; if they're already offering an absurdly good price; or if you like the person, make an offer closer to the asking price.
Ebay's "make an offer" system has a straightforward provision for them to say, "no thanks, how about $Y."
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