Faced with a tough new opponent, Leslie and Ben disagree on the content of her first campaign ad. Ron is very uncomfortable when Chris tries to befriend him, while Andy and April make a trip to the doctor.

It's Valentine's Day and Leslie decides she needs to find Ann a new man. Ben must enlist Ron's help when he is stumped by Leslie's elaborate Valentine's Day scavenger hunt, and Chris is depressed about the status of his love life.