'Grey's Anatomy' Star Patrick Dempsey Nearly Got Divorced From His Wife After 20 Years

It all started when the actor booked a haircut at her hair salon. At first, she figured it was another joke by her prankster employee.

“All the people he had written in were names of celebrities famous in the ’80s, like Molly Ringwald,” she told People. 

"I was shocked [when he came in for an appointment] but at the same time, I was happy because he was so cute,” Jillian recalled. 

When they married in 1999, it wasn’t Dempsey’s first trip down the aisle. When he was 21, he got married to his best friend’s mom — yes, really. 

When their age gap inevitably became an issue for the pair, they divorced six years later. 

"People wind up going through two different cycles in their lives.”

His second marriage to Fink was much more successful.

They were together while both of their careers took off, with Dempsey finding massive success on Grey's Anatomy and other films, and Fink nabbing big celebrity clients.

In January 2015, Fink filed for divorce, citing “irreconcilable differences.” A statement by the couple read, “It is with careful consideration and mutual respect that we have decided to end our marriage. Our primary concern remains the wellbeing of our children, and we ask with profound gratitude that you respect our family’s privacy at this very sensitive time.” 

"They were never going to make it work, but they tried.” With Patrick's star power rising, the couple reportedly struggled with not being able to spend that much time together.

By the end of that year, they were photographed looking in love and holding hands in Paris.

Sacrifices clearly had to be made to make their marriage with, starting with Dempsey leaving Grey's.

He also cut back his time at the race track, which was a huge passion of his.

“Our marriage was not something I was prepared to let go of,” he told People. “I didn’t feel like we had done all the work. And we both wanted to do that work. That’s where it started.”

Love that!