The proliferating gig economy relies on online freelance marketplaces, which support relatively anonymous interactions by text-based messages. Informational asymmetries thus arise that can lead to exchange uncertainties between buyers and freelancers. Conventional marketing thought recommends reducing such uncertainty. However, uncertainty reduction and uncertainty management theories indicate that buyers and freelancers might benefit more from balancing, rather than reducing, uncertainty, such as by strategically adhering to or deviating from common communication principles. With dyadic analyses of calls for bids and bids from a leading online freelance marketplace, this study reveals that buyers attract more bids from freelancers when they provide moderate degrees of task information and concreteness, avoid sharing personal information, and limit the affective intensity of their communication. Freelancers’ bid success and price premiums increase when they mimic the degree of task information and affective intensity exhibited by buyers. However, mimicking a lack of personal information and concreteness reduces freelancers’ success, so freelancers should always be more concrete and offer more personal information than buyers do. These contingent perspectives offer insights into buyer–seller communication in two-sided online marketplaces; they clarify that despite, or sometimes due to, communication uncertainty, both sides can achieve success in the online gig economy.