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In the books Stefan did his best to please their father, while Damon ran rampant, womanizing and dropping out of university. As Italian nobles, this reflected badly on the family and Damon got in a lot of trouble.

Since Stefan was well behaved and dedicated, their father hoped for his marriage to Katherine, a German noble, and tried to keep her away from Damon.

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Q: Did Stefan and Damon Salvatore ever get in trouble with their dad?
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