Minimizing the spread of Human Immunodeficiency Virus (HIV) is one of the primary goals of any public health system. Couple testing is one of the strategies that is widely used in achieving this goal. In our study we sought to determine factors that predispose couples to acquiring HIV. Secondly, we also wanted to quantify the amount of risk of HIV infections couples were willing to tolerate when initiating new sexual relationships. This study was done at the Mary Immaculate VCT Center Nairobi, from 2012 to 2018. A total of 360 couples was recruited into the study using systematic random sampling technique. A couple comprised of two persons of opposite gender who came for VCT services. In this study we observed that only 45.3% of the respondents engaged in sexual affairs within marriage compared 54.73% who did not. We also observed that the mean age difference within couples was 2.4 years and those who had an age difference of 3-5 years were more likely to engage in pre-marital sex. In addition, we also found that that 86.1% of the couples had engaged in sexual affairs without knowing the HIV status of their partner(s). We conclude that most couples were engaging in premarital and extramarital sex than in marital sex. Sex outside marriage is a risk factor that contributes to acquisition and spread of HIV. An average of 2.4 years was the age difference preferred by most study couples. Age difference is a factor that facilitates transmission of HIV from one generation to another. We also concluded that most couples in this study preferred having sex first before knowing their HIV status. This is a risky practice that facilitates new acquisition of HIV infection.