Positive social connections improve wellbeing. Technology increasingly affords a wide variety of media that people can use to connect with others, but not all media strengthen social connection equally. Optimizing wellbeing, therefore, requires choosing how to connect with others wisely. We predicted that people's preferences for communication media would be at least partly guided by the expected costs and benefits of the interaction-specifically, how awkward or uncomfortable the interaction would be and how connected they would feel to their partner-but that people's expectations would consistently undervalue the overall benefit of more intimate voice-based interactions. We tested this hypothesis by asking participants in a field experiment to reconnect with an old friend either over the phone or e-mail, and by asking laboratory participants to "chat" with a stranger over video, voice, or text-based media. Results indicated that interactions including voice (phone, video chat, and voice chat) created stronger social bonds and no increase in awkwardness, compared with interactions including text (e-mail, text chat), but miscalibrated expectations about awkwardness or connection could lead to suboptimal preferences for text-based media. Misunderstanding the consequences of using different communication media could create preferences for media that do not maximize either one's own or others' wellbeing. (PsycInfo Database Record (c) 2021 APA, all rights reserved).