During the COVID-19 pandemic several behavioral measures have been implemented to reduce viral transmission. While these measures reduce the risk of infections, they may also increase risk behavior. Here, we experimentally investigate the influence of face masks on physical distancing. Eighty-four participants with or without face masks passed virtual agents in a supermarket environment to reach a target while interpersonal distance was recorded. Agents differed in wearing face masks and age (young, elderly). In addition, situational constraints varied in whether keeping a distance of 1.5 m required an effortful detour or not. Wearing face masks (both self and other) reduced physical distancing. This reduction was most prominent when keeping the recommended distance was effortful, suggesting an influence of situational constraints. Similarly, increased distances to elderly were only observed when keeping a recommended distance was effortless. These findings highlight contextual constraints in compensation behavior and have important implications for safety policies.