mess with (one's) head

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mess with (one's) head

To cause someone to feel confused, exasperated, frustrated, or anxious. All the rules and regulations with this business are really starting to mess with my head. I don't know why you have to mess with his head like that. If you don't want to be in a relationship with him, just say so!
See also: head, mess

mess with someone's head

cause someone to feel frustrated, anxious, or upset. US informal
See also: head, mess