Owing to the extremely narrow beams, a main issue in optical deep space communications is represented by miss-pointing errors, which may severely degrade the system performance and availability. In this paper, we address pointing losses in the case in which both the receiver and the transmitter are affected by angular errors. Pointing losses are evaluated through two approaches. The first approach is deterministic and only requires knowledge of a maximum angular error. The second approach requires knowledge of the angular error statistical distribution and tackles the problem from an outage probability viewpoint. These tools are then applied to analyze the impact of pointing losses in deep space optical links in which both terminals suffer from miss-pointing effects. The antenna gains are first optimized to maximize the effective system gain. The optimum antenna gains are then applied to evaluate maximum achievable ranges and to perform link design by means of optical link budgets.