When a chick, who is usually fat, gets skinny, then fat than skinny again. But she always ends up fat for a while, suffering from not being able to stay skinny. Named for Oprah's constant wait loss and eventaul regain.
Ted: That cow Hillary is fat again! She was skinny last week!
Pat: Poor bitch has Oprah Winfrey's Disease! She can't keep the wait off.
Pat: Poor bitch has Oprah Winfrey's Disease! She can't keep the wait off.
by APT October 13, 2005

by Bapty August 10, 2009

by WITTYMOFO December 4, 2013

a way to say that's another story entirely; similar to can of worms; back in the day when the oprah show was all shock television one day it would be cheating husbands the next it'd be drug-addicted prostitutes
Y: Our boss is such a dumbster!
X: Did you hear about him asking out the new secretary???
Y: Yes...don't get me started!!! That's a whole other Oprah.
X: Did you hear about him asking out the new secretary???
Y: Yes...don't get me started!!! That's a whole other Oprah.
by absolutely April 13, 2008

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

by carrie jackson May 15, 2018
