To pay for Stewie's private school, Lois becomes a postal worker. She finds a letter from Peter that was never sent to his old fling, Gretchen (guest voice Kathryn Hahn), dated a week before their marriage. When Gretchen tries to come between Lois and Peter, Lois has a plan of her own.

To everyone's surprise, Chris wins homecoming king. However, Meg finds out that the cool kids plan to prank him during the homecoming ceremony, so they go to the school to investigate. Meanwhile, Cleveland starts hanging out with Jerome, the bartender. So Peter and the guys try to replace him.