When a fat, ugly woman with a lot of money still looks like Oprah Winfrey. It doesn't matter how many face lifts or fancy clothes or jewelery she wears, she still looks like the maid or the cook.
That woman suffers from the Oprah Syndrome, she has a lot of money but she still looks like the fat smelly maid.
by Mikey Boyer July 2, 2011
If you disclose anything bad about your life, a person with Oprah Winfrey Syndrome will say they had it happen to them too. One day a guest on the Oprah show disclosed being sexually molested Oprah disclosed that it had happened to her too. Another day a guest disclosed using Cocaine, and Oprah said she did too. I'm not saying that Oprah and other's with this condition are lying, but they always seem to have a story of hardship that is equal, if not worse, than the one you just told.
here is an example of the Oprah Winfrey Syndrome
Suzy: I don't know what I'm going to do I just lost my job.
Pam: Girl, I just lost my job too, and I found out I'm not eligible for unemployment!
Suzy: I don't know what I'm going to do I just lost my job.
Pam: Girl, I just lost my job too, and I found out I'm not eligible for unemployment!
by FLINGSHOT September 20, 2013