Naomi Watts | 40

Actress and producer Naomi Watts found love with fellow Hollywood star, Live Schreiber, with whom she has two children. Their first son was born while Watts was in her late thirties, and by the time she hit her forties, she gave birth to their second child. They were both proud parents of her two boys and wished that she could have more children with Schreiber.

Though the two did not get married, they stayed together for 11 years before announcing they were already in the process of separating. They did remain amicable for the sake of their two sons, whom they are co-parenting to this day. Watts has moved on from that breakup and is now with Billy Crudup. Even though her career has slowed down somewhat, the actress has enough investments to support her family and give her children what they want and need.