In the 1987 romantic comedy, Can’t Buy Me Love, Dempsey played the nerdy teenager Ronald Miller, who had to pay for pretending a girlfriend.

Years later, the star re-emerged in the medical drama, Grey’s Anatomy as the dreamy doctor whose death caused a meltdown with his die-hard followers.

Though Dempsey hinted in 2013 that he might be leaving the show, Entertainment Weekly reported in 2014 that he and co-star Ellen Pompeo, who plays

Meredith, signed a new two-year contract, which gave the good doctor at least until 2016.

Little was known about Dempsey’s departure from the hit series and even those of us who had never seen the show, were left wondering “why?”

According to reports, Dempsey, the father of three, hit his breaking point and started acting out on the set of the show.

In an interview for the book, How to Save a Life: The Inside Story of Grey’s Anatomy (2021), Dempsey confessed to resenting the Grey’s schedule. “It’s 10 months, 15 hours a day. You never know your schedule, so your kid asks you, ‘What are you doing on Monday?’ And you go, ‘I don’t know,’ because I don’t know my schedule,” Dempsey said. “Doing that for 11 years is challenging. But you have to be grateful, because you’re well compensated, so you can’t really complain because you don’t really have a right.”

And, what happened early 2015 might explain his on-set behavior.

On January 23, 2015, Radar Online delivered some breaking news with a story that said, “McDreamy is about to be on the market!”

Dempsey, also a professional race car driver, was at a 24-hour race event in Daytona Beach, Florida, when Jillian Fink, his wife of 15 years at the time, filed for divorce.

To make things right, Dempsey left his role as Dr. McDreamy and focussed on his role as a husband and father. He told People that the potential end of his marriage was “scary.”

“Our marriage was not something I was prepared to let go of. I didn’t feel like we had done all the work. And we both wanted to do that work. That’s where it started.” He continued, “It’s always destabilizing when you’re potentially breaking up a family or you have a big section of your life that’s ending.”

Like the scripts to the romcoms he stars, his love story with Jillian has a storyline filled with laughter, sadness, hope and of course a lot of love.

In 1994, when Dempsey was 28, he walked into the Delux salon and met his stylist Jillian Fink, who was also the owner.

A 2002 story published in People, recounts their meeting.

Dempsey called the salon to make an appointment and when Fink saw his name scheduled in the book, she believed it to be a prank from an employee.

Dempsey earned celebrity status from his roles in Can’t Buy Me Love and Loverboy (1989) and she was surprised when he walked through the salon door for a haircut.

“I was shocked,” Fink recalls of that moment. “But at the same time, I was happy because he was so cute.”

However, like Sweet Home Alabama (2002) the romcom he stars with Reese Witherspoon, their relationship was complicated by another partner. Dempsey and Jillian were both in relationships and after three years of haircuts and conversation, the pair finally came together.

The couple was married in 1999 at his family’s farmhouse in Maine, an intimate ceremony where Kristen Mason, the bride’s sister and business partner, said, “He saw her and started crying.”

The 2000’s were promising for the pair, both who enjoyed successes personally and professionally.

Following a series of box office fails, Dempsey’s slump came to an end with roles in Scream 3 (2000), Grey’s Anatomy (2005-2015), Made of Honor (2008) Valentine’s Day (2010), and Bridget Jones’s Baby (2016).

Jillian, after spending six years as Avon’s global creative color director, is now a celebrated makeup artist, with a client list that includes many Hollywood celebrities.

The pair are parents to daughter Talula, born in 2002, and in 2007 their family of three grew to five with twins Sullivan and Darby.

Now, focusing on family, he quit racing, which he started in 2004, but still holds an interest with Dempsey Racing.

“Everybody has their own path,” says Dempsey, now 57. “Jill and I decided it was time to work on our issues and improve. We wanted to be role models for our kids like, okay, if you have differences, you can work them out.”

He added, “You can only do one thing at a time and do it well,” he says. “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.”

In 2016, they called off the divorce and in 2023, the couple celebrates their 24th wedding anniversary. On February 4, Dempsey posted a loving and funny birthday message on his Instagram, which reads, “Wishing my amazing, beautiful, talented, crazy funny wife happy birthday. This was the expression when she started to count the candles on her cake catching her in all her glory-happy birthday! You’re like a fine wine, you only get better with age. Have a great birthday. Love you always.”

What a sweet love story!

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