Patrick Dempsey and his wife, Jillian Fink, recently celebrated a significant milestone: the high school graduation of their twin sons, Darby and Sullivan. The proud parents shared heartfelt messages and rare family photos to commemorate the occasion.(people.com)
On May 30, 2025, Dempsey posted a photo on Instagram featuring himself, Jillian, and their 18-year-old sons dressed in matching navy-blue graduation robes. The family was all smiles as they marked the twins’ graduation from Crossroads School for Arts & Sciences in Santa Monica, California. In the caption, Dempsey wrote, “Graduation!! So proud of you boys and cannot wait to see where the next chapter of your lives will take you!” (people.com)
Jillian also shared a photo of the twins with their arms around each other, captioning it, “CONGRATULATIONS CLASS OF 2025! I am such a proud momma. Life’s next chapter is upon us—go get it, my sweet boys! Love you both to the moon and back.” (pagesix.com)
Darby and Sullivan, born on February 1, 2007, have grown up largely out of the public eye. However, they made a rare red carpet appearance with their family at the premiere of the film “Ferrari” in December 2023. Fans were struck by the striking resemblance between Darby and his father, with some dubbing him “the next McDreamy,” a nod to Dempsey’s iconic role on “Grey’s Anatomy.” (lifeandstylemag.com, rorue.com)
The twins have distinct personalities: Darby is known for his reserved and quiet demeanor, while Sullivan is recognized for his humor and expressive nature. Dempsey has shared that Darby has a passion for soccer, and he has coached his son’s team. Sullivan, on the other hand, has shown an interest in acting, a path his father supports. (people.com, lifeandstylemag.com)
Dempsey and Fink, who married in 1999, also have a daughter, Talula Fyfe, born in 2002. Talula graduated high school in 2020 during the COVID-19 pandemic, which led to the cancellation of traditional senior year events. To make up for the missed experiences, Dempsey organized a “mock prom” at home for his daughter, allowing her to celebrate with friends virtually. (pagesix.com, thelist.com, businessinsider.com)
In recent years, Talula has pursued her passion for baking, launching her own business, Talula’s Kitchen, in 2024. She studied at Le Cordon Bleu culinary school in Paris and London and worked as a pastry chef at Gucci Osteria in Beverly Hills. (people.com, parade.com)
Despite the challenges of raising children in the public eye, Dempsey and Fink have focused on providing a supportive and nurturing environment for their family. They briefly separated in 2015 but reconciled the following year, crediting open communication and mutual effort in mending their relationship. They celebrated their 24th wedding anniversary in 2023 and continue to appear united with their children at public events. (people.com, pagesix.com)
As Darby and Sullivan embark on the next chapter of their lives, their parents’ pride and support are evident. The family’s recent celebrations highlight the strong bonds and shared milestones that continue to define the Dempsey family’s journey.(people.com)
