In Washington, DC, the leading mode of HIV transmission is through men who have sex with men (MSM) behavior. This study explored differences between frequent HIV testers (men testing at least twice a year) and annual or less frequent testers (men testing once a year or less) in DC. Nearly, one-third of MSM reported testing for HIV at least four times in the prior two years. In the multivariable model, frequent testers had significantly higher odds of being aged 18-34 (aOR =1.94), knowing their last partner's HIV status (aOR=1.86), having 5+ partners in the last year (aOR=1.52), and having seen a health-care provider in the last year (aOR=2.28). Conversely, frequent testers had significantly lower odds of being newly HIV positive (aOR=0.27), and having a main partner at last sex (vs. casual/exchange partner; aOR=0.59). Medical providers need to be encouraged to consistently offer an HIV test to their patients, especially those who are sexually active and who have not tested recently.