Adolescent romantic experiences can have profound developmental significance and may be predictive of future romantic relationships. Despite such potential significance, little is known about the challenges that confront teenage boys when navigating dating relationships. The present study sought to understand how masculine gender norms influence boys' attitudes and behaviors and the influence of cultural expectations as they anticipate prospective dating relationships. Focus-group discussions were held with adolescent boys (N = 23), ranging in age from 14 to 18 years, from a multicultural Canadian city. Grounded Theory methodology was used to analyze discussion responses. The Central Category of the grounded theory was "Anticipating Getting Experience in Dating," while communicating and benefiting from relationships were subcategories. "Masculine Gender Norms" arose as the major Contextual Category. The findings demonstrate how these boys attempted to maintain a socially approved masculine status while coincidingly struggling with confidence and the demands of this status. Contextual factors involving peer expectations, social/digital media culture, multicultural context, and parents' expectations additionally contribute to their navigational struggles. Implications for boys' relational development, in light of masculine gender norms, are addressed. Interventions are suggested to support boys in their development of confidence in romantic communications.