This chapter discusses some of the basic tenets of therapy with men as they relate to the topic of tears in therapy. It then presents a case to examine the unique challenges that can accompany therapists' tears with male clients. Men often resist coming to therapy even when they know they need help. When a man comes in for a consultation, the situation tends to be relatively extreme. While the presentation of an issue may be described in a calm manner, underneath there is often fear, anxiety, and shame. When Zack came to treatment, the author assumed he would have trouble accessing his emotions. Zack was 35 years old and recently divorced, with a 13-year-old daughter who was living with his ex-wife. When Zack shared his story about finding his mother dead, it was the turning point in their therapy, the emergence of the theme that helped them understand so many other aspects of Zack's world.