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Introduction: Research suggests that social disconnection is one pathway that explains why perfectionists have higher negative mental health outcomes. However, thus far research has not examined the role that perfectionists' expectations, about their social world, plays in explaining social disconnection. The current study examined whether negative expectations about future social events and social hopelessness explained the relations between socially prescribed perfectionism (SPP), self-oriented perfectionism (SOP), and social disconnection. Method: The current study used experience sampling methodology (ESM) with 145 participants to test multilevel structural equation models examining whether negative expectations and social hopelessness mediated the relation between SPP (as well as SOP) and loneliness at the following time point. Results: Results indicate that having negative expectations for future social interactions and feeling socially hopeless explains the relation between SPP and loneliness both when loneliness was measured concurrently and loneliness measured later in the day. Having lower levels of social hopelessness explained the relation between SOP and loneliness when loneliness was measured concurrently and later in the day. Discussion: Findings suggest that SPP and SOP are differently associated with cognitions about social interactions and relationships in daily life, which in turn explains variations in loneliness. Results indicate that targeting socially prescribed perfectionists’ negative social cognitions in treatment may be effective for reducing loneliness.