In the substantial body of research on gender differences in the initiation of negotiation, the findings consistently favor men (Kugler et al., 2018). We propose that this research itself is gendered because negotiation research has traditionally focused on masculine negotiation contexts. In the current study, we replicate the gender effect in initiating negotiations (favoring men) and provide an empirically based selection of “masculine,” “feminine,” and “neutral” negotiation contexts, which can be used for future negotiation research. We show that the negotiation context shapes gender differences such that in specific social contexts, women tend to have even higher initiation intentions compared to men. Negotiation contexts generally seem to differ regarding their affordance to negotiate. We offer a possible explanation for gender effects on initiation intentions by uncovering the mediating role of expectancy considerations across all negotiation contexts, especially in masculine contexts, and instrumentality considerations in specific masculine and feminine contexts.