Is singer Aubrey O’Day hiding something about her alleged affair with Donald Trump Jr., who reportedly fell head over heels for her? O'Day first shot to fame as a member of the girl band Danity Kane in the early 2000s. She later appeared on season 5 of ‘Celebrity Apprentice’ in 2011. According to published reports, Don Jr., who appeared on the show as a guest judge, was smitten with the singer. "He told her it was over with his wife,” a source told US Magazine.