I like negotiating. I’ve gotten discounts and items earlier than most because of negotiating.

The trick to negotiating is to have an idea of who the person is, and what s/he wants. Phrase your request/desire in a way that makes it seem not like a favour, but that it’s very small and the person may even benefit (example: “Oh I would be so happy if a rep could do this for me! He’d hear great feedback from me!”

There are other times I will not be so nice. I have to call Paypal soon because as a seller, I got scammed with a chargeback and they haven’t really done anything. Then, you must be firm but respectful, and (in my case) add a subtle hint of legal threat. When disputing something with the company, make sure you already know their TOS and you haven’t violated it. Think of the excuses the person will come up with and think of comebacks.

It takes alot of skill and complete accuracy to be a negotiator. as @seekingwolf said, you don’t want to make someone feel cheated while you try and bargain for something your trying to get. Weather it be Free stuff or a discount. Finesse is key. My advisor once got the humane society to give him a puppy at a discounted rate… of 50%. i was both shocked and admired his craft.

I negotiate everything from furniture to jewelry. Jewelry will usually have a 400% markup or higher and is always negotiable.