Demi Moore and Ashton Kutcher — Ashton Kutcher began dating Demi Moore, who is 15 years his senior, in 2003, after Moore and Bruce Willis had an amicable parting. Kutcher and Moore wed on September 24, 2005, in a small Kabbalah-oriented ceremony. The way they were so playful and loving in public, you never sensed that their union was in peril until it imploded on impact when Kutcher was caught cheating on their sixth wedding anniversary.