Patrick Dempsey & Wife Jillian Celebrate Their Twin Sons' Graduation With Sweet Photos

Patrick Dempsey shared a rare glimpse into his personal life as he celebrated the high school graduation of his twin sons along with his wife, Jillian.

Patrick Dempsey is celebrating a major family milestone. The "Grey's Anatomy" star took to Instagram to share that his twin sons, Darby and Sullivan Dempsey, have graduated from high school.

In a rare family photo posted online, Patrick is seen with his wife, Jillian Dempsey, and their sons, all dressed in graduation caps and gowns. "Graduation!! So proud of you boys and cannot wait to see where the next chapter of your lives will take you!" he captioned the post, expressing both pride and excitement for the future.

The post quickly drew a wave of fan reactions, with many offering congratulations and marveling at the family's striking resemblance. "Wow, the DNA is strong on that family! Congratulations boys, from your Maine peeps," one fan wrote. Another added, "Wow, what a good looking family."

Commenters also chimed in on how closely the twins resemble their parents. "They got his original nose," one person noted. Another echoed the sentiment, saying, "One looks like dad and the other looks like mom." "It's crazy how one looks exactly like their mom and one looks exactly like their dad," agreed a netizen.

A more detailed observation followed, "I think everyone is saying that one looks like dad and one looks like mom simply because of the hair. The blonde actually looks more like Patrick. Both twins have Patrick's mouth but his face looks more like Patrick's, while the dark-haired one has Jillian's cheekbones. Both twins actually have Patrick's small mouth."

A few fans summed it up with playful comparisons, writing, "Jillian and Sullivan are twins and Patrick and Darby are twins." However, not everyone agreed on the likeness. "Don't look alike at all," one user commented. Another added, "They look fine but they don't look at him at all. [sic]"

The graduation celebration comes just months after another milestone. Back in February, the "Enchanted" star marked the twins' 18th birthday with a heartfelt Instagram post. "happy birthday boys. Love you. I can't believe you're 18 !!! [sic]" he wrote, alongside a sweet tribute to his sons.

Jillian also took to Instagram to show her sons some love. Alongside photos of the pair with their backs to the camera, she joked, "This is what 18 year olds will allow their mom to post for their birthday 😅 Already 1 foot out the door or 4 feet out the door.[sic]"

"Happy 18th birthday to my boys Sullivan & Darby. You’ll always be my babies 🖤 I love you both!" she concluded.

While Patrick rarely shares photos of his family on Instagram to maintain their privacy, Jillian has featured her children on her own page multiple times. One time, she proudly shared a clip of herself playing with Darby's hair.

The clip starts with Darby greeting viewers as his mother, Jillian Dempsey, plays with his hair. "You getting your hair done?" she asks. "Yeah, it’s nice," he responds.

"What's in it, do you know?" Jillian asks, to which Darby replies, "Dandruff," drawing laughs from his mom and the behind-the-scenes crew.

Jillian then lets Darby and the audience know that the product in his hair is Roadie and Roomie mix. "Look at how gorgeous it's looking," she observes.

Jillian wasn't the only one who thought her son’s hair looked incredible, as fans flooded her comment section with compliments. "Darby is so good looking & has his dad's gorgeous hair! Lucky young man," one fan wrote. Others marveled at how grown up he'd become, as one viewer exclaimed, "Wow, your son is so big and handsome!!"

"So handsome! So grownup!" said another. Others couldn’t help but notice Darby's resemblance to his father, Patrick Dempsey. One person observed, "Looks just like his dad❤️." "He looks like Patrick!!!!" another said.

Some saw both Jillian and Patrick in Darby, as one viewer stated, "Darby is the perfect mix of you and hubby ❤️." "Darby looks exactly like Patrick 😍," swooned another.

It's not the first time Jillian did Darby's hair. In August 2024, not long before schools reopened, she shared a short video showing the result of a haircut she had just completed.

The products she mentions in the first clip above are from her self-named beauty brand, which also caters to men. Jillian often enlists the help of her family to model for—and even help improve—her merchandise.

"I will always try everything on my family members, and I absolutely welcome any and all feedback. I incorporate this if I think it plays a role in what I have set out to create," she shared during a joint 2022 PEOPLE interview with her husband.

Just days before she showcased the results of her Roomie and Roadie mix on Darby's hair, the mom of three had her kids flaunt more of her products.

She posted a short carousel of Darby and his sister, Talula Fyfe Dempsey, modeling the Jillian Dempsey lipgloss and spot stick. "Family business 🤌," she captioned simply.

Darby is one of three kids born to quite the power couple. He and his fraternal twin brother, Sullivan, took their first breaths on February 1, 2007. The pair came after their older sister, Talula, who was born in 2002.

Shortly after they were born, Patrick offered a small glimpse into their growing family life and the difference between Darby and Sullivan’s personalities.

"Sullivan will probably read this article in 20 years and say, 'What did you say about me?' He's sort of the grumpy old man. Darby is very much the peaceful, quiet little Buddha," the actor reflected.

In addition to a soft-spoken nature, Darby seems to enjoy sporty activities and being outdoors. When he was around nine, his dad shared he had a passion for soccer. At the time, Patrick was also his coach.

Darby's Instagram profile also reflects his interest in sports and nature. In February 2024, he went snowboarding in Mount Baldy, California, and posted a thread of photos and videos showcasing his prowess in the sport.

In the previous year, in September, he participated in the Dempsey Challenge hosted by the non-profit organization Dempsey Center. The Challenge is an annual walk/run/ride event that raises funds for people impacted by cancer.

"100% of funds raised by Challenge participants helps provide personalized, holistic services AT NO COST to cancer patients, their loved ones, and care partners," the website states. Since its inception, this event has raised over $18 million for the Dempsey Center.

Among the thousands of athletes that had attended and contributed, Darby and his dad chose to ride.

Darby's siblings have also been paving their own paths career wise. When he was younger, Patrick shared that Sullivan wanted to be an actor. Talula, on the other hand, loved cooking, and it's a passion she has followed wholeheartedly.