Scientific studies demonstrate high rates of HIV infection among male-to-female (MTF) transgender individuals and that stigma and discrimination place MTFs at increased risk for infection. However, there is little research examining how gender roles contribute to HIV risk. This paper reports on in-depth interviews with 20 MTFs attending a community clinic. Data reveal that stigma and discrimination create a heightened need for MTFs to feel safe and loved by a male companion and that in turn places them at a higher risk for acquiring HIV. Male-to-female transgender individuals appear to turn to men to feel loved and affirmed as women; their main HIV risk stems from their willingness to engage with sexual partners who provide a sense of love and acceptance but who also may also request unsafe sexual behaviours. A model illustrating how HIV risk is generated from stigma and discrimination is presented.