Rob Lowe and Sheryl Berkoff – 30 YEARS

Rob Lowe was one of the hottest Hollywood personalities back in the day. The heartthrob has a sea of admirers but he has his eyes set on the ever-so-gorgeous Sheryl Berkoff, a celebrity makeup artist. Due to his smoldering good looks and impeccable skills in acting, Rob wasn’t exactly a one-woman type of guy. All of that changed when he met Sheryl. She made an honest man out of him, because almost 30 years later after they got together in 1990, they are still madly in love with each other.

Their first meeting didn’t really scream infatuation for both because Sheryl was dating one of Rob’s friends, Emilio Estevez. However, on the set of Bad Influence, they met again. It was 1990 and things were different — they finally went on a date. Like every couple, they had their fair share of ups and downs but they powered through. They tied the knot on July 22, 1991. Now, they have two sons in their twenties, Matthew and John, both of whom aren’t just as handsome as their old man, they are extremely smart too. Both earned a degree after finishing college.