This study examined the relationship between male gender role conflict (J. M. O'Neil, 1981) and willingness to seek help for depression and substance abuse from a variety of potential helpers in a sample of U.S. and Costa Rican men. Results revealed variability in men's willingness to seek help across both culture and type of helper. Restrictive emotionality and restrictive affectionate behavior between men were related to decreased willingness to seek help from several helpers, whereas success, power, and competition were positively related to help-seeking ratings for some targets (Internet, mothers) and negatively related to ratings for male friends. These results suggest that the relationship between masculine gender socialization and help-seeking behaviors may depend on a variety of factors surrounding different problems and help-seeking opportunities.