As brands solidify their place in social media environments, consumers' expectations have amplified, thus spurring the development of technologies to assist with the engagement process. Understanding the ways in which brands can preserve the one-to-one characteristics and intimate relationship qualities offered by social media while still meeting consumer expectations amidst the escalating volume of interactions has become essential. Drawing on the communications literature, this research proposes that parasocial interaction (PSI) theory may be used as a theoretical lens for designing successful social media strategies. Three studies, using a multi-method approach, provide evidence of PSI's role in the development of positive relationship outcomes. Mediation analysis reveals that this sense of feeling connected with the brand goes beyond the interaction itself and drives increased feelings of loyalty intentions and willingness to provide information to the brand. Evidence from this research suggests that these effects may not hold when consumers are aware of the possibility that the brand's social media response may be automated. These findings offer marketers theoretical guidance for fostering relationships in social media environments.