Like his Grey's Anatomy character, Derek Shepherd AKA McDreamy, Patrick Dempsey has also been married twice. When he was 21, he married Rocky Parker, then-47-year-old mother of his best friend. They were married for 7 years. They had a messy divorce which was finalized in 1994. Parker had accused the actor of domestic abuse but later withdrew the allegations in 2006. She died in 2014 from throat and lung cancer.

Dempsey's second and current wife is Jillian Fink. The couple met during the actor-turned-racer's divorce battle. It wasn't until 1997 that they made things official. In 1999, the two tied the knot at his farmhouse in Maine. Then 16 years into the marriage and three kids later, the two announced that they were getting a divorce but reconciled after a year. Here's the real reason they almost called it quits.

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The Picture Perfect Marriage

Both of their careers took off when they got married. Dempsey landed his most recognized role in Grey's Anatomy while Fink became one of the most sought-after makeup & hair artists in Hollywood — with clients like Julia Roberts and Bradley Cooper. She also started her own beauty brand, Jillian Dempsey, where she has a line of lip & cheek tints, eyeliner, hair pomade, and more.

The Can't Buy Me Love actor even joked: "We try not to get into each other’s work too much. My big thing is to make sure the lipsticks taste good when you kiss. And, well, so far they taste pretty darn good." It all seemed to be working out so well. They had booming careers, plus their three wonderful kids ​​​​​​— Talula Fyfe, 19, and 14-year-old twins, Darby Gallen and Sullivan Patrick. But in 2015, Fink filed for divorce citing "irreconcilable differences."

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The Truth Behind Their 'Irreconcilable Differences'

The couple released a joint statement, saying: "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."

TMZ also reported that the makeup artist wanted joint custody of their children, plus spousal and child support. Later on, it was revealed that she'd filed for divorce due to the Enchanted star's lack of time. Back then, the actor was juggling hectic work schedules in Grey's Anatomy and in the racetrack.

Dempsey started racing in 2004. At the 2014 German Grand Prix, he said: "I couldn't imagine not racing right now. It really keeps me motivated. It's all I think about on a daily basis."

In 2016, when the two were spotted together again, he finally decided to leave Grey's Anatomy. He left in season 14. "It had been long enough," he told People. "It was time for me to move on with other things and other interests. I probably should have moved on a couple of years earlier." Apparently, it was also a choice he had to make to save his marriage.

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Working On Their Marriage

"You have to work at everything," Dempsey told Evening Standard. "And you cannot do everything. Something has to be sacrificed." Leaving Grey's Anatomy and replacing his racing sessions with family time were a great start for the couple. Even though he's grateful that the series "has given [him] the opportunity to do everything," the actor said that it still came with "a cost." He said that "no matter how much money you make, you want control out of your own schedule."

Luckily, the couple hadn't fully given up after Fink had filed for divorce. After a few talks, they both decided to try and work things out. "Our marriage was not something I was prepared to let go of," Dempsey said. "I didn’t feel like we had done all the work. And we both wanted to do that work. That’s where it started."

The couple worked out their differences with the help of a marriage counselor. "You can only do one thing at a time and do it well," the actor said about his realizations from that time in their marriage. "I [learned] to prioritize. Our union has to be the priority. I wasn’t prepared to give up on her and she wasn’t either. We both wanted to fight for it."

After finding their way back to each other, Fink filed to have the divorce papers dismissed in November 2016 — the same time Dempsey had officially bid farewell to Grey's Anatomy. It was a "new beginning for the couple." In July 2021, they celebrated the 22nd year of their marriage.

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