Anne has made an excellent summary above. I see it exactly the same way. This all may be similar to those previous experiences when the T told you that he does not ruminate over what happens in your therapy and about the details of your relationship nowhere near as much as you do, and many other people also do not. Perhaps these different scenarios are manifestations of the same tendency driven by anxiety and doubts that you have specifically, maybe not that unique as some people express here periodically that they have similar reactions. But many other do not and may get surprised when you bring them up. This is how accepting what others say at face value is a better approach, especially others who have already proven themselves to be reliable. I don't have the same tendencies as you regarding relationships and interpersonal interactions but something similar regarding the quality of my own performances and whatever I produce, especially professionally. I tend to second guess and and come up with potential trouble spots endlessly unless I really force myself to stop and truly consider external feedback. It usually helps me tremendously when I trust and accept externals not not just the content and processes of my restless mind. Having a penetrating perception and attention to details and how things (and people) harmonize can be a powerful ability but can also drive one crazy when anxiety distorts it.
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