It really is awkward to socialize with your superior. On one hand, building a good relationship with them can be beneficial. On the other hand, it feels strange because a genuine friendship usually involves little to no filtering. With a superior, however, your livelihood is at stake, so you’re constantly trying to gauge whether a topic is a potential landmine that could negatively affect your career. It often feels like you’re walking on eggshells. On top of that, it’s difficult to shake the suspicion that they might be socializing with you partly to monitor or evaluate you. While that isn’t always the case, some team leads do cross professional boundaries, and when they do, many organizations seem to respond with little more than a slap on the wrist, despite the privacy concerns such behavior can raise.