Distributing long-tail content is a difficult task due to the low amortization of bandwidth transfer costs as such content has limited number of views. Two recent trends are making this problem harder. First, the increasing popularity of user-generated content and online social networks create and reinforce such popularity distributions. Second, the recent trend of geo-replicating content across multiple points of presence spread around the world, done for improving quality of experience (QoE) for users. In this paper, we analyze and explore the tradeoff involving the "freshness" of the information available to the users and WAN bandwidth costs, and we propose ways to reduce the latter through smart update propagation scheduling, by leveraging on the knowledge of the mapping between social relationships and geographic location, the timing regularities and time differences in end user activity. We first assess the potential of our approach by implementing a simple social-aware scheduling algorithm that operates under bandwidth budget constraints and by quantifying its benefits through a trace-driven analysis. We show that it can reduce WAN traffic by up to 55 percent compared to an immediate update of all replicas, with a minimal effect on information freshness and latency. Second, we build TailGate, a practical system that implements our social-aware scheduling approach, which distributes on the fly long-tail content across PoPs at reduced bandwidth costs by flattening the traffic. We evaluate TailGate by using traces from an OSN and show that it can decrease WAN bandwidth costs by as much as 80 percent and improve QoE. We deploy TailGate on PlanetLab and show that even in the case when imprecise social information is available, it can still decrease by a factor of 2 the latency for accessing long-tail YouTube videos.