Is there a syndrome related to chronic conflictiveness and trick questions?

My last conversation with my mom went like this... I said something to her. She said it was stupid and said something else. I agreed with her. She said it was stupid and said something else.

My last conversation with my dad... He owns access to my bank account. He can see all my transactions. He asks me if I made a specific transaction that he couldn't have identified without looking it up. He knew I made the transaction. Apparently he wants to test me to see if I'll tell him the truth even though he knows I know I'll never get away with lying to him and therefore never try.

Do these reflect mental illnesses? Or are they just very difficult people to have a relationship with?

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I doubt that what you have described reflects any known mental health problem.

To me it says more about your relationships with both of your parents than anything else.

Best wishes.