Despite increased global interaction, difficulties in communication due to cultural differences and language proficiency must be negotiated (Varonis and Gass, 1985a; 1985b). Therefore the present study looked at how native and non-native English speakers interacted, with a particular focus on native/native conversations. Using a within-subjects design, native/native, non-native/native and non-native/non-native pairs undertook a map task where one participant directed the other along a predetermined route, negotiating ambiguous stimuli. Each participant then completed a questionnaire rating their own and their partner’s English proficiency. It was predicted that non-native/non-native pairs would take the longest and negotiate the most, whilst native/native pairs would do the opposite. The timings and number of words used per group and per director/matcher were analysed using ANOVAs, and proficiency ratings were assessed also. Finally, the checking for understanding data (Pica, Young & Doughty, 1987) was analysed both quantitatively and qualitatively. The results showed that the non-native pairs took the longest to negotiate, whilst the non-native/native pairs took the least time and used the fewest words. Furthermore, non-native directed pairs checked for understanding more often. Although the proficiency and checking for understanding data were not significant, qualitative analysis revealed interesting differences between the three conditions nonetheless, and presented ideas for future research for facilitating such conversations.