U.S. immigration question

Re: U.S. immigration question

Yeah he's going to talk to some professional about his situation. But I wanted to get some ideas beforehand.
Since he has prolonged his stay beyond 6 months, do you think they will let him come back even though his visa would still be valid for few more years? If he's allowed to reenter, would he have a clean record when his wife-to-be applies for his immigration?