Prior to their lavish 1994 nuptials, Angelil served as Dion’s manager. The former singer was 38 when he discovered the Canadian singer, then 12. Angelil would go on to mortgage his home in 1981 just to fund her first album. The two turned their business relationship into a romantic one and went on their first official date in 1987, when she was 19 years old. In 1990, they posed together backstage at The Tonight Show.