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Look for friction. Look for work-life imbalance. Observe how the person displays emotion to others. Consider how the person responds to emotions in others.

Article:
People with OCPD do not restrain themselves from imposing their ideas and views on others, even in situations where most other people would consider such behavior inappropriate. The idea that this kind of attitude and behavior could upset people and lead to friction in relationships often does not occur to them, nor will it stop them from doing what they intend to do.  A person with OCPD is not likely to feel guilty when crossing the boundaries even if it means monitoring, controlling, meddling and intruding into other people’s lives so that there is perfection and order in everything. They get upset, angry and depressed if other people are not following their directions. They may become angry or frustrated if it seems like people are not aligned with them in their effort to bring everything under control and to make everything perfect. People with OCPD generally spend a considerable part of their waking hours at work—and they do it by choice. They are hardly left with any time for leisure. Their leisure time, if any, is spent on trying to “improve” things. Because of this, the person may not have many (or any) friendships.  If a person with OCPD tries to spend his/her leisure time on a hobby or some activity such as painting or some sports such as tennis, s/he does not paint or play for the fun of it. S/he is constantly in the pursuit to master the art or the game. S/he will apply the same theory to family members and expect them to set out on a pursuit to excel rather than trying to have fun.  This interference and meddling gets on the nerves of the people around them. This not only ruins the leisure time but can cause damage to relationships. For most people with OCPD, emotions are a waste of precious time that could be otherwise used in their quest for perfection. They are generally very tight-lipped when comes to expressing or displaying feelings.  This reticence is also due to a worry that any expression of emotion must be perfect; a person with OCPD will wait for an extremely long time to say anything to do with feelings in order to make sure that it is “just right.”  People with OCPD may come across as stilted or overly formal when they try to display their feelings. For example, they may try to shake hands when the other person goes in for a hug, or use overly stiff language in an effort to be “correct.” People with OCPD not only have trouble expressing emotion, they also have difficulty tolerating its presence in others. People with OCPD may visibly display discomfort in a situation where people are emotional (such as at a sporting event or family reunion).  For example, most people would likely consider greeting a friend whom they haven’t seen in awhile as an exciting, emotional experience. A person with OCPD may not experience it this way, and might not even smile or offer a hug. They may seem to feel “above” emotions and look down on people who display them as “irrational” or inferior.