This article examines how social serendipity has developed and been transformed in professional networking communicative practices that previously were predominantly in person and are now also digitally mediated through LinkedIn, videoconferencing, and virtual reality. Using a linguistic ethnographic approach, I apply Björneborn’s (2017) theory of serendipity that posits three broad affordances: (1) diversifiability, the ability to meet heterogeneity; (2) traversability, the ability to explore; and (3) sensoriability, the ability to perceive through the senses. Data come from projects on professional networking practices from 2017 through 2023, and include ethnographic observations, interviews, and recorded networking events. Findings show mediating technologies have significantly transformed aspects of the face-to-face networking process, with changes in serendipity, linked to environmental affordances of diversifiability, traversability, and sensoriability. Existing theorizations explain many underlying fundamental aspects of human communication that shape our interactions with humans but newer frameworks are needed to account for the intersection with technologies.