Negotiating your bills - Don't be shy! Ask for a discount.

I read this CNN Money article today and it rang true with me. A dear friend who has insurance with an astronomical out of pocket (oh the joys of self-employment!) told me in the past that she ultimately negotiated down a medical bill by offering to pay a lower amount of it in cold, hard cash. Her strategy paid off and she was able to save a few hundred dollars off the bill.

I'm not sure if I would stick it to my drycleaner, though. If I were a loyal customer, I wouldn't hesitate to ask them if they advertise discounts that I may not be aware of - such as in a newspaper I do not read or perhaps even in a ValPak mailing I wouldn't get. But it doesn't hurt to ask. I wouldn't do it every time, but I do think there's some value in being flexible with pick up times.

Have you even negotiated down a bill? If you have, please share your money saving strategies here. In recent months, I have asked for a signficant discount on a damaged item and had a manager relent. The worst they could say is no, so ask away!