So here's a scene you don't see too much anymore: brightly lit grocery store, customer with a cart full of items, shopkeeper running the items through the scanner when the customer says, "Five dollars a pound for those cantaloupes is pretty expensive. Would you take three?"
Gone are the days when you could dicker with the shopkeep when buying ponchos.
Why don't we see that anymore? Because it doesn't work it huge supermarkets. You can't haggle your way down with a cash register clerk. You can't even do it with the manager at the chain store supermarkets. It would be, in a word: ridiculous. Not only would it never work, it would embarrass everyone around you, particularly loved ones.
However, there are still an entire world of situations in the modern world where you can haggle. And sometimes you just have to go looking for them. Great opportunities for this exist at farmer's markets, antique stores, thrift stores, garage sales, craigslist.com offers and really any small business where the owner of the business is the person you're talking to. Non-chain service stores such as repair shops, contractors, and design/art studios are perfect examples of this.
There are two basic strategies involved in the art of the haggle:
"Its Not Personal; It's Business." For this mindset you have to believe that you aren't taking advantage of this person, you're simply getting the best price both of you can afford to give. They want your business, and you don't want to pay more than you have to. To this end, you can comparison shop, ask for better prices using competitor's advertisements and offers, and interact with these businesses as if you were getting bids on a construction contract, for example. Act as if the entire operation is a business transaction, not a personal one, and this can be very successful. However, this is not the best tactic with extremely personal sellers, such as artists and garage salers.
"Quick and Painless." For the more personal business transaction (think, buying a knicknack at a garage sale or a spur of the moment purchase) follow a few guidelines. If the price is $35 and you want to pay $20, offer $15 and be prepared for them to lower the price to $25. Counteroffer $20 or pay the $25 if you feel it is a fair price. The key to this type of tactic lies in the details. Have your cash ready so that you don't need change, as this just increases awkward downtime during the transaction. Don't be afraid to note something that might be wrong with the item or another reason to justify lowering the price. ("Do you have the missing kickstand for this bike anywhere? No? Oh, well would you take $20 for it then?")
2/3rds of the time, this will probably work, and the truth is that people would rather be offered deals that they have the power to say no to then never sell their item. So be fearless and confident. And never try to haggle if it makes you feel bad (in a developing country, from your relatives, etc.)
Try it - it can't hurt!