Ouch. Donald Trump Jr. was reportedly cheating on his pregnant wife with an 'Apprentice' contestant until his father told him to 'cut it out' Donald Trump Jr., allegedly cheated on his wife with a contestant on "Celebrity Apprentice" for months while his wife Vanessa was pregnant with their third child, Page Six and Us Weekly reported. Trump Jr. met singer Aubrey O'Day after she appeared on his father's reality show, which he was on as an adviser. The pair began their relationship in late 2011 as the taping of the show was wrapping up, and it continued until March 2012, according to Us Weekly. "When it started, they were very serious all of a sudden," a source told Us Weekly. "He told her it was over with his wife, that they were separated and he didn't love her. … Aubrey fell for him hard. She thought they were going to be together for real."