Jake's date with Brandy was a total disaster. Everything went wrong. The time was wrong. They were polar opposites in every way. A snafu on Serena's side caused the mistake. They both wondered what Serena was thinking.
Chris walks in on his girlfriend and best friend since boy scouts having sex. Serena sets him up with a woman who doesn't want to have a relationship. No commitments, no emotions, no hurt feelings.