Basically, willpower isn't magic, and humans can't precommit.
A sufficiently good social character can, with sufficient effort, convince you of something absolutely ridiculous. It's not too different from running into a really, really good used car salesman.
AI Box Experiment Update #3
Tuxedage (AI) vs Alexei (GK) - Gatekeeper Victory
Tuxedage (AI) vs Anonymous (GK) - Gatekeeper Victory
I have won a second game of AI box against a gatekeeper who wished to remain Anonymous.
This puts my AI Box Experiment record at 3 wins and 3 losses.