For Valentine's Day, Raymond has the fake diamond in Debra's engagement ring replaced with a real one. He doesn't realize Debra already had it replaced with a diamond from her grandmother's ring.

When Ray is up for Sports Writer of the Year Award, he becomes overly pessimistic about winning. When Debra convinces him to be more optimistic, he discovers that has a downside when the rest of the family is full of pessimists in their own right.