Purpose -The purpose of this paper is to explore the role of humor in online negotiations and assess whether humor can act as a bridge for the otherwise relationship-poor experience of negotiating via e-mail. Design/methodology/approach -Two experimental studies are conducted, using 122 executive MBA students and 216 MBA students respectively. Findings -Study 1 demonstrates that beginning an e-mail transaction with humor results in: increased trust and satisfaction levels; higher joint gains for the dyad; and higher individual gains for the party who initiated the humorous event. Analyses reveals that it is the exploration of compatible issues (as opposed to effective tradeoffs) -that increased the level of joint gain. Study 2 demonstrates that first offers in a purely distributive negotiation are more likely to be within the bargaining zone when e-negotiations are initiated with humor, and the resulting final settlements in the humor condition are also more equally distributed between parties (more of an "even split") than are transactions without a humorous start.Research limitations/implications -The highly controlled laboratory setting (the classroom) limits the generalizability and encourages future research in a more real-world setting. Practical implications -Managers may benefit by making personal connections in the online realm before engaging in professional communications, such as strategically employing humor at the outset of e-mail negotiations. Originality/value -This is the first study to empirically explore the direct role of humor in online negotiations a controlled experimental setting, and find its positive effects on the negotiation process.