1) I constantly tell him to stop but he doesn’t want to listen to me. He might hurt himself one of these days.
2) He should spend more time reading in Italian rather than in Spanish.
I would make the sentences brief: I constantly tell/keep telling him to stop but he doesn't listen. He may get hurt one day. He should spend more time reading Italian than Spanish.
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I would make the sentences brief:
I constantly tell/keep telling him to stop but he doesn't listen. He may get hurt one day.
He should spend more time reading Italian than Spanish.
Tom