Sadness fits the facts when there is a loss. This may be loss of something the person had, or loss of something they anticipated having. There are two phases to sadness: The first is to withdraw, and the second is actively seeking what has been lost. This might involve rekindling reminders of it or seeking out something similar to replace it. This chapter discusses the signature features of sadness and presents an example scenario of sadness. It highlights special considerations in regulating sadness. In sadness the therapist’s use of down-regulation should be sparing. The development of self-validation, and the ability to sit with justified sadness is important. Signs that clients are blocking sadness are: holding their breath, excessive swallowing, pressing lips together tightly, or blinking away tears.