<p>Contemporary career development increasingly unfolds through fragmented and uncertain transitions, making university career fairs potentially important spaces for early career exploration and meaning-making. However, despite their widespread use, career fairs are often understood primarily through recruitment or satisfaction-oriented frameworks, offering limited insight into how students and employers jointly experience and interpret these encounters as relational career events. Addressing this gap, the present study employed a dual-perspective phenomenological design to examine how relational meanings are constructed through brief student–employer interactions at a university career fair. Semi-structured interviews were conducted with 20 participants (13 university students and 7 employer representatives) following a large-scale university career fair in Türkiye. Data were analyzed inductively using Moustakas’s transcendental phenomenological procedures. Findings revealed a pronounced interactional asymmetry: students approached the fair through a relational–developmental orientation, seeking dialogue, guidance, and recognition, whereas employer representatives operated within a strategic–organizational logic emphasizing visibility, talent cultivation, and selective engagement. This divergence, compounded by structural constraints such as crowding and time pressure, produced a transactional void in which students’ dialogic expectations frequently encountered procedural responses. A preparation paradox also emerged, whereby students’ visible preparatory efforts often failed to align with employers’ implicit expectations regarding career clarity and intentional engagement. By conceptualizing career fairs as relational career contexts rather than merely recruitment events, this study contributes to theoretical discussions of career development as a relationally constructed process and offers practical implications for designing career fairs that better support students’ career exploration and development.</p>