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Patrick Dempsey attends a red carpet for the movie "Ferrari" at the 80th Venice International Film Festival on August 31, 2023 in Venice, Italy. (Photo by Maria Moratti/Getty Images)© Getty Images

Grey's Anatomy star Patrick Dempsey shares rare picture of wife and lookalike twin sons as they graduate

Patrick is known as McDreamy in Grey's Anatomy

Rebecca Lewis
Los Angeles correspondent
May 31, 2025
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Grey's Anatomy star Patrick Dempsey has celebrated a momentous occasion, as his youngest twins have graduated high school.

"So proud of you boys and cannot wait to see where the next chapter of your lives will take you!" Patrick captioned a post on Instagram that featured a gorgeous family picture of his sons Sullivan and Darby in their caps and gowns, standing between their mom, Jillian, and dad.

Patrick Dempsey and wife Jillian pose with sons Darby and Sullivan at their graduation© Patrick Dempsey
Patrick Dempsey and wife Jillian pose with sons Darby and Sullivan at their graduation

High school graduation

Darby also shared the picture, revealing that he "couldn’t have asked for a better senior year" alongside a carousel that included a picture with sister Talula and one of Darby receiving his diploma on stage.

The siblings graduated from the Crossroads School for Arts & Sciences in Santa Monica, California.

Their older sister Talula, 22, was also in attendance and she commented on the post with a series of hand emojis, while mom Jillian wrote how "proud" she was of her "baby".

Talula Dempsey and Darby Dempsey pose at his high school graduation
Talula and Darby pose at his high school graduation

Sullivan took to Stories to reshare a post from a friend that showed Sullivan posing with a group of girlfriends standing on the steps of the school.

Unique qualities

"They all have unique qualities and they have their own goals that they need to develop and harvest themselves and we just try to model our behavior and hopefully they’ll pick up on that," he previously told People magazine of his children.

“They need to find out how they interact in the world, they need to learn those boundaries, they need to make mistakes. And you need to be there for them and allow them to learn from that,” the actor added.

Patrick Dempsey (L) and Jillian Fink attend the premiere of Neon's "Ferrari" at Directors Guild Of America © FilmMagic
Patrick (L) and wife Jillian in 2023

26 years of marriage

Patrick and Jillian married in 1999 but in 2015 she filed for divorce. They later reconciled and called the divorce off 22 months later.

Patrick was a teen star but found lasting fame when he starred alongside Reese Witherspoon as her fiance in the 2002 movie Sweet Home Alabama.  

Grey's Anatomy

He joined the cast of Grey's Anatomy in 2005 as Dr Derek Shepherd – also known as McDreamy – alongside Ellen Pompeo, Sandra Oh, Katherine Heigl, Justin Chambers, T. R. Knight, Chandra Wilson, James Pickens Jr and Isaiah Washington.

Ellen Pompeo as Dr. Meredith Grey and Patrick Dempsey as Dr. Derek Shepherd© Disney General Entertainment Con
Patrick starred as Dr. Derek Shepherd in Grey's Anatomy

McDreamy was the love interest for Dr. Meredith Grey (Pompeo), whom the show revolved around as it chronicled her progression from surgical intern to fully-qualified doctor to the hospital's chief of general surgery.

He was on the show for ten years before he was killed off in 2015 after marrying Meredith and welcoming two children together; she was pregnant with their third when he died in a car accident.

Jillian Dempsey's sweet Valentine's tribute to husband Patrick Dempsey

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