Although you are interested in understanding the owner better, you already understand the most important aspects of his personality, namely that he is private, work oriented, and uninvolved and even uninterested in his employees' personal lives. This does not make him a bad person or a bad manager. It merely makes him who he is.
If he had wanted to open the doors to his personal life and yours, he would have done so at some point over the past four years. He is obviously comfortable and satisfied with the present level of communication on this matter.
If you are satisfied with the opportunities to achieve, earn, grow, and advance here, and your working relationship with this individual is positive and productive in all other aspects, you should put this matter on a back burner. However, if this matter is gnawing away at you, invite your manager to lunch and tell him about an off-the-job accomplishment by you or a member of your family. In this way, you are speaking his language by focusing on an accomplishment, while at the same time opening the door for a discussion of non-work topics. His reaction and response will tell you if off-the-job topics are permanently off limits.
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