For “Grey’s Anatomy” fans, April 23, 2015, was a heartbreaking day—the moment Dr. Derek Shepherd, played by Patrick Dempsey, was ki.lled off the show.
Though it wasn’t a real-life tragedy, devoted viewers were left stunned by the sudden loss of the beloved “McDreamy.”
Dempsey first gained recognition in the 1987 romantic comedy “Can’t Buy Me Love”, where he played a nerdy teenager who paid a girl to pretend to be his girlfriend. Years later, he re-entered the spotlight as the charming neurosurgeon in “Grey’s Anatomy”. His character’s unexpected departure after a decade-long run left many wondering why he left.
Though Dempsey had hinted in 2013 that his time on the show might be coming to an end, reports in 2014 suggested he had signed a two-year contract extension, making his exit in 2015 all the more surprising.
However, behind the scenes, Dempsey was struggling. He found the show’s grueling schedule—ten months of filming, often with 15-hour workdays—overwhelming, especially as it kept him from spending time with his children.
Tensions reportedly rose on set, and Dempsey admitted in “How to Save a Life: The Inside Story of Grey’s Anatomy” that the demanding schedule took a toll on him. “You never know your schedule, so when your kid asks what you’re doing Monday, you have to say, ‘I don’t know.’” While he acknowledged how fortunate he was, he also admitted that balancing work and personal life was becoming increasingly difficult.
At the same time, his personal life was unraveling.
On January 23, 2015, “Radar Online” broke the news that Dempsey’s wife of 15 years, Jillian Fink, had filed for divorce. At the time, he was at a race event in Daytona Beach, Florida. The couple’s marriage was in trouble, and the fear of losing his family forced Dempsey to re-evaluate his priorities.
Determined to save his relationship, he chose to leave “Grey’s Anatomy” and focus on his role as a husband and father. He later admitted to People that the thought of ending his marriage was “scary.” He and Jillian both felt there was still work to be done in their relationship, and they weren’t ready to give up on each other.
Dempsey and Jillian’s love story began in 1994 when he walked into Delux, her salon. At the time, Jillian, a celebrity hairstylist, thought it was a prank when she saw his name on the appointment book. But when Dempsey showed up for a haircut, she was pleasantly surprised. Their relationship didn’t begin immediately—both were involved with other people. However, after three years of haircuts and conversations, they finally got together.
The couple married in 1999 in an intimate ceremony at Dempsey’s family farmhouse in Maine. Jillian’s sister, Kristen Mason, recalled that when Dempsey saw his bride, he immediately started crying.
The early 2000s were a successful time for both.
Dempsey revived his acting career after a series of box office disappointments, landing roles in “Scream 3” (2000), “Grey’s Anatomy” (2005-2015), “Made of Honor” (2008), “Valentine’s Day” (2010), and “Bridget Jones’s Baby” (2016). Meanwhile, Jillian became a renowned makeup artist and spent six years as Avon’s global creative color director.
The couple welcomed their daughter, Talula, in 2002, and their twin boys, Sullivan and Darby, in 2007. As their family grew, so did their challenges. Dempsey had also taken up professional race car driving in 2004, a passion that, along with his acting career, contributed to the strain on his marriage.
However, in 2016, after putting in the effort to rebuild their relationship, Dempsey and Jillian called off their divorce. He also stepped away from racing to prioritize his family, realizing that relationships require dedication and effort.
Now 57, Dempsey continues to focus on his family and marriage. In 2023, the couple celebrated their 24th wedding anniversary, proving that their love, like a great romcom, had its challenges but ultimately endured. Dempsey’s heartfelt birthday message to Jillian on Instagram captured their journey perfectly: “Wishing my amazing, beautiful, talented, crazy funny wife a happy birthday… You’re like a fine wine, you only get better with age.”
