Some people that I know use this joke. A lot. Every chance they get, in fact.
There's a book called That's What She Said. [Link] (It's actually a book about poetry or something.)
Steve Carell pretty much beat the joke to death on purpose and ironically because his character on the show is awkward and lame. (Here's a collection of Michael Scott's "That's what she said" joke from The Office.)
Here's an amusing wiki about how to be annoying: http://www.wikihow.com/Make-Lame/Dry-Jokes
Here's a video. [Link]
My opinion: the joke sucks. It requires very little thought, if any. I know people who have used this joke so many times that even when it is used cleverly, its humor is just lost in the din of the million other "that's what she said" jokes that were already told that day, and sucked.