This study examined gender differences in relationships among vocational skills, motivational approaches, and same-gender and cross-gender interests for urban adolescents. Results showed gender differences in interests, with males having greater Realistic interests and females having greater Artistic and Social interests, based on Holland's (1997) theory of interest types. Structural equation modeling revealed that males tended to approach the occupational world with assertiveness, the desire to create opportunities, and the use of instrumental support. Females tended to approach the occupational world by being adaptable, capitalizing on their skills and abilities, actively preparing themselves for the future, exploring options, and using emotional support. Recommendations for career development practice are provided. (Contains 1 table and 2 figures.)