The complexities of dating are exacerbated when couples’ getting together happens with the support of another person – the disability support worker. This paper explores the experience of Vic, a worker whose role it was to drive a couple to their dinner or movie dates. Vic’s narrative prompts consideration of how such workers position themselves within the sometimes conflicting role demands of enabler, risk manager, and mentor, negotiating the emotion work and relationship mediation roles they may be expected to perform. His narrative reveals the event as a performance of normalization, surveillance, management and othering, emotion work and feeling rules, and recognition.