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I am sucker for over analyzing situations, so I sympathize with the OP and his friend. Over analyzing and looking for faults is not a happy way to live. The key for me is to realize that enjoying something that is Good Enough right now is better than waiting for a hypothetical Perfect thing that may or may not exist. This could apply to a decision on which route to take to work, which camera to buy, or who to spend Friday night with.
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