Counseling patients through their journey to conceive can be challenging. When a therapist becomes pregnant, the therapeutic alliance alters.This chapter explores the unique dynamics between the pregnant fertility counselor and reproductive clients. Questions around the “who, what, where, when, why and how” of pregnancy disclosure are used as a tool to help think about the various elements to the therapeutic alliance. Intense feelings can be triggered for a patient who is struggling with infertility or pregnancy loss, but can also trigger emotional reactions for the fertility counselor. The transference and countertransference that arises with the self-disclosure of a pregnancy is likely to unfold complicated dynamics and emotions. The positive and negative implications that a pregnancy disclosure can have from the patient’s point of view, as well as that of the therapist, are addressed. Additionally, the postpartum experience and the return back to work after parental leave are also discussed. While this chapter focuses on the pregnant therapist, the issues raised pertain to all pregnant reproductive medical staff treating infertility patients.