The McDreamy Twins: What Patrick Dempsey's Sons, Sullivan And Darby, Are Doing After Their 2025 Graduation
Patrick Dempsey's twin sons, Sullivan Patrick Dempsey and Darby Galen Dempsey, have officially stepped into the spotlight of adulthood, marking a major milestone in May 2025 with their high school graduation. This event, celebrated privately but shared publicly by the proud actor, signifies a significant transition for the sons of the 'Grey's Anatomy' star and his wife, celebrity makeup artist Jillian Fink. The focus now shifts to what the 18-year-old twins plan to do next as they navigate life outside the protective bubble of one of Hollywood's most enduring families.
As of late 2025, the world is watching to see if the Dempsey twins will follow their father's path into the arts, their mother's into beauty and entrepreneurship, or forge a completely new identity. Patrick Dempsey has often spoken about the challenges of raising children in Hollywood, noting that his sons are determined to establish an identity separate from his massive "McDreamy" shadow. The recent graduation from the prestigious Crossroads School for Arts & Sciences in Santa Monica suggests a strong foundation for whatever path they choose.
The Complete Dempsey Family Profile: Sullivan and Darby's Biography
Patrick Dempsey and his wife, Jillian Fink, share a life that has spanned over two decades, resulting in three children. The twin boys, Sullivan and Darby, represent the second set of children for the couple, arriving a few years after their older sister. While Patrick Dempsey is globally recognized for his acting and racing career, his children have largely maintained a life out of the constant media glare, allowing them a relatively normal upbringing in Los Angeles.
- Mother: Jillian Fink (Celebrity Makeup Artist, Entrepreneur, and Co-Founder of JDM Racing)
- Father: Patrick Galen Dempsey (Actor, Racing Driver, and People's 2023 Sexiest Man Alive)
- Older Sibling: Talula Fyfe Dempsey (Born February 20, 2002)
- Twin Son 1: Sullivan Patrick Dempsey
- Twin Son 2: Darby Galen Dempsey
- Date of Birth (Twins): February 1, 2007
- Current Age (Twins in 2025): 18 years old
- Place of Birth: Los Angeles, California
- High School: Crossroads School for Arts & Sciences, Santa Monica (Graduated May 2025)
The Major 2025 Milestone: High School Graduation
In May 2025, Patrick Dempsey took to social media to share a rare family photo celebrating the high school graduation of both Sullivan and Darby. The milestone marked the end of their foundational education at Crossroads School, a private institution known for its focus on arts, sciences, and a long list of celebrity alumni.
The proud father shared his congratulations, emphasizing the magnitude of the achievement. This public acknowledgment was notable because the Dempsey family is generally reserved about sharing details of their children's lives. The twins, dressed in their graduation robes, stood with their parents and older sister, Talula Fyfe Dempsey, in a picture that quickly garnered attention from fans of the 'Grey's Anatomy' icon.
For celebrity children, a high school graduation is more than just an academic achievement; it's a public signal of their transition into independent young adults. This event now opens the door to their next chapters, whether that involves higher education, pursuing professional interests, or taking a break to travel the world.
Stepping Out of the 'McDreamy' Shadow: Personality and Interests
While the Dempsey twins have maintained a low profile, their father has offered subtle glimpses into their individual personalities and interests over the years. This desire for privacy aligns with Patrick Dempsey's own comments about his parenting philosophy.
Patrick Dempsey has stated that raising children in the intense environment of Hollywood is "very challenging." He noted that all three of his children, including Sullivan and Darby, are keen to have their "own identity, separate from me and that shadow." This suggests that any future career paths or public roles they take on will likely be on their own terms, distinct from their father's acting fame.
Sullivan Patrick Dempsey: The Funny Twin
Patrick Dempsey once revealed a small, charming detail about Sullivan, describing him as "very funny." The actor noted that Sullivan has a unique way of expressing himself, with "funny expressions in the way he's talking." This suggests a lighthearted, expressive personality, perhaps hinting at a potential interest in creative or performance arts, which would be well-supported by his education at the arts-focused Crossroads School.
Darby Galen Dempsey: The Private Twin
Details about Darby Galen Dempsey are even more scarce, indicating a preference for a highly private life. His middle name, Galen, is the same as his father's middle name (Patrick Galen Dempsey), a subtle nod to the family connection. While specific interests are not public, the twins are known to be active. Patrick Dempsey has credited his teenage sons with helping him maintain his fitness and active lifestyle, which is crucial for his demanding professional racing career. This shared interest in physical activity and health may be a strong bond between the father and his twin sons.
The Future: College, Careers, and The Dempsey Legacy
The most pressing question following the May 2025 graduation is what lies ahead for Sullivan and Darby. As of the end of 2025, neither Patrick Dempsey nor Jillian Fink has publicly disclosed their sons' post-high school plans. This continued discretion is a clear sign that the family is committed to protecting the twins' right to choose their future without public pressure.
There are several potential paths for the twin brothers:
- Higher Education: Given their attendance at a top-tier preparatory school, it is highly likely that one or both twins will attend a university. The lack of an announcement could simply mean they are attending a school outside of the celebrity media's usual focus, or they have chosen to take a gap year.
- The Arts: Graduating from an arts-focused school suggests a strong interest in creative fields, such as film, music, or visual arts. They may choose to pursue a path behind the camera or in a non-acting creative role, minimizing their public exposure while still working in the industry.
- Motorsports and Entrepreneurship: Patrick Dempsey’s passion for auto racing is a massive part of his life, and he has involved his family in his racing team, Dempsey Racing. Both twins have been seen at racing events, and this could be a shared passion. Furthermore, their mother, Jillian, is a successful entrepreneur in the beauty industry. Either of these fields—motorsports management or business—could be a natural fit for the twins as they start their careers.
Regardless of their individual choices, the Dempsey twins represent the next generation of a high-profile Hollywood family. Their journey to forge their own path—whether it leads to the halls of academia, the world of business, or a quiet, private life—will be the defining narrative of their early adulthood. Their father, who was named People's Sexiest Man Alive in 2023, has shown nothing but support for their independence, ensuring that Sullivan Patrick Dempsey and Darby Galen Dempsey will be known for their own merits, rather than just as 'McDreamy's sons.'
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