Both male-to-female transsexuals and advanced prostate cancer (PCa) patients are treated with androgen-suppressing drugs that have emasculating effects. Additionally, transsexuals take estrogenic compounds to feminize their bodies. We explore the quality of life of these populations, based on interviews with 12 individuals from each group. Overall, the transsexuals had a better psychological response to chemical castration than the PCa patients. The transsexuals showed more enthusiasm about the changes in their life; they viewed their lives as beginning anew, accepted their reduced libido, and were more comfortable with their increased emotionality. Different responses in the two groups are not surprising given that they undergo androgen deprivation under very different medical contexts. However, the fact that the transwomen are able to conceptualize the effects as positive suggests that some androgen-deprived PCa patients may benefit from reconceptualizing their changes within a positive framework. Additionally, difference in the two populations may be attributed, in part, to the fact that the transsexuals take supplemental estrogen. Circumstantial evidence suggests that estrogen in androgen-deprived males may improve sleep quality, help retain sexual interest, and protect cognitive function. This suggests that PCa patients may benefit from using estradiol for androgen suppression.