At a Glance
- Patrick Dempsey and Jillian Dempsey celebrate a 25-year marriage.
- They met in 1994 at her salon, married in July 1999, and have three children.
- Jillian is a celebrated makeup artist who launched two brands.
- Why it matters: Their enduring partnership showcases resilience and mutual support.
Patrick Dempsey and Jillian Dempsey have celebrated a series of milestones together, from Patrick’s 60th birthday surprise to the premiere of his new series, Memory of a Killer, in January 2026. Their story, which began in a Los Angeles salon, illustrates how love, career, and family can intertwine over decades.
Meeting and Early Years
The couple first crossed paths in 1994 when Patrick walked into Jillian’s hair salon as a client. Jillian, then a rising hairstylist, was surprised to see his name on a list of high-profile customers that an employee had humorously compiled. She later recalled, “I was shocked, but at the same time, I was happy because he was so cute.”
They began dating in 1997, after both were already in other relationships. Patrick’s first date with Jillian was a homemade meal at his home, and she moved in just three months later. Their romance developed while Jillian continued to build her career in hair and makeup.
Marriage and Family
After two years of dating, the couple tied the knot in July 1999 during a farmhouse wedding on a family property in Maine. According to Jillian’s sister, Patrick shed a few tears when his bride walked down the aisle.
They welcomed three children:
- Daughter Talula Fyfe (born 2002)
- Twin sons Sullivan Patrick and Darby Galen (born 2007)
In July 2024, the couple celebrated a 25-year marriage. Patrick posted a heartfelt tribute on Instagram, writing, “Life would not be the same without you… your sexiness, your intelligence, your warmth, your friendship.”
Professional Lives
Jillian’s Makeup Empire
Jillian Dempsey broke into the industry in the early 1990s and quickly became known for her skill as a hairstylist and makeup artist. She sold her Los Angeles salon in 1998 and went on to create a signature lip gloss for the Charlie’s Angels cast, with her products later featured in the 2002 rom-com Sweet Home Alabama.
She has cultivated a star-studded client roster that includes Kristen Stewart, Kate Winslet, and Emma Roberts. Jillian’s influence extends beyond individual clients; she launched two makeup brands:
- Delux Beauty – a line focused on hand-applied products.
- Her eponymous cruelty-free, organic, and vegan line launched in 2014.
In a 2021 interview with Beauty Independent, Jillian explained, “With my first brand Delux Beauty, I couldn’t afford to do anything that was natural. The cost of goods would have been too high. I wanted to make my current brand cruelty-free and vegan, utilizing natural and organic materials where I could find ingredients and making it really easy to use.”
Patrick has been a supportive partner, even modeling for Jillian’s products. On March 30, 2023, Jillian posted a video of herself applying Patrick’s moisturizer and fixing his hair, thanking him for being a “fun model on our shoot days.”
Patrick’s Acting and Racing
Patrick Dempsey is best known for his role as Derek Shepherd, “McDreamy,” on Grey’s Anatomy. Outside of acting, he is an avid car racer and was named News Of Los Angeles‘s Sexiest Man Alive in 2023, a title Jillian celebrated publicly on Instagram.
Milestones and Public Moments
- Patrick’s 60th Birthday (2026): Jillian surprised him on the set of Memory of a Killer, posting a video on Instagram.
- Venice Film Festival (August 2023): The couple attended the premiere of Patrick’s film Ferrari. Jillian made a statement in a white A-line dress paired with a leather jacket, while Patrick wore a black tuxedo.
- Sexiest Man Alive Announcement (2023): Jillian posted, “Well, the cat’s out of the bag for 2023 @people’s #SexiestManAlive and my hubz is on the cover!”
Challenges and Resilience
In January 2015, the couple briefly split, and Jillian even filed for divorce. They spent the year in couples therapy, privately repairing their marriage. Patrick later told News Of Los Angeles, “Everybody has their own path. 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 described their reunion as a “new beginning,” emphasizing communication, openness, and the importance of not giving up. Patrick added, “You can only do one thing at a time and do it well.”
Personal Touches
Jillian admits she loves being makeup-free despite her profession. In an interview with Maine Women Magazine, she shared, “I would hate for them to remember me as ‘in a mirror doing your makeup.’ I think that is why I like to do everything on the vanity front as condensed and fast as possible. I call it ‘lazy girl makeup.'”
Family involvement is integral to Jillian’s product development. She says she always tests her cosmetics on family members and welcomes feedback. Patrick once remarked, “My big thing is to make sure the lipsticks taste good when you kiss. And, well, so far they taste pretty darn good.”
Takeaways
- Patrick and Jillian’s 25-year marriage showcases the power of partnership, resilience, and shared goals.
- Jillian’s transition from hairstylist to successful makeup entrepreneur demonstrates innovation and commitment to cruelty-free beauty.
- Their public celebrations-Patrick’s birthday surprise, the Ferrari premiere, and Jillian’s Instagram posts-highlight their deep bond.
- The 2015 near-split and subsequent therapy underscore the importance of communication and mutual effort in long-term relationships.
- Jillian’s focus on family feedback and “lazy girl makeup” reflects a balance between professional ambition and personal authenticity.
Their journey offers a compelling narrative of love, career, and family that resonates beyond the silver screen.
