#4: Oprah Winfrey

Age: 70

Relationship Status: in a relationship with Stedman Graham since 1986

Oprah Winfrey and Stedman Graham’s 30-year relationship, which began in 1986, is an iconic testament to enduring love in the ever-changing Hollywood landscape.

Decades before meeting Stedman in 1986, Oprah faced the tragic loss of her son, who died the same year he was born. She has remained childless since, once noting her children would dislike her if she had any.