This graduation season, Patrick Dempsey and his family are celebrating the high school graduation of his youngest sons, twins Sullivan and Darby, who just completed Crossroads School in Santa Monica. In a recent picture the Grey's Anatomy star shared, I was knocked out by what I noted in the frame. (Don't forget, he's People magazine's 2023 "Sexiest Man Alive.")
Patrick Dempsey Posts Surprise Photo of Twin Sons—and It Made Me Do a Double Take
Proud Papa salutes his boys
Published Jun 1, 2025
•6:43pm
Gilbert Flores/Variety via Getty Images
"So proud of you boys and cannot wait to see where the next chapter of your lives will take you!" writes Dempsey alongside a photo of him, Darby and Sullivan, and their mom Jillian Dempsey grinning between the boys.
Here's my takeaway—not only is the family beautiful, but the twins' looks are evenly divided between their gorgeous parents. Darby's strong jaw and nose favor the handsome features of his father, as does the thicket of wavy dark hair framing his face. Sullivan, by contrast, has a narrower face with high cheekbones and a delicate mouth—like his mom, who is professional makeup artist Jillian Dempsey. (She's been married to their actor dad since 1999.) And Sullivan's silky blond mane? That's all mom.
Arnold Jerocki/FilmMagic/Getty Images
Dempsey's toothy smile reflects the relaxed and enthusiastic vibe that the actor spontaneously busts out when he's involved with his offscreen passion—automobile racing. He and his wife just visited Europe for the F1 Grand Prix of Monaco, for example, where he was all smiles and gave a thumbs-up as he waved the checkered flag in the race. Along with racing, it's the Maine native's love of family and friends that keep him bouyed.
JC Olivera/FilmMagic/Getty Images
In fact, the last public appearance of the whole Dempsey clan occurred when the family—including now-22-year-old Talula, older sister to the twins—showed up at the premiere of Ferrari. In this Michael Mann biopic, Dempsey inhabited the role of Italian racer, sportsman and engineer Piero Taruffi. At the late 2023 premiere, just as at 18 months later at their high school graduation, you can spot the strong family resemblance of the youngest Dempsey children.
Lucky boys—good genes, diplomas and a movie star dad.
