Patrick Dempsey Shares ‘Proud’ Moment At Twin Sons’ Graduation

Aug 05, 2025 by apost team

Actor Patrick Dempsey, renowned for his role as Dr. Derek “McDreamy” Shepherd on “Grey’s Anatomy,” celebrated a significant family milestone in May 2025: the high school graduation of his twin sons, Darby and Sullivan Dempsey. Patrick, 59, was in full dad mode as his twin sons walked across the graduation stage. The ceremony took place at Crossroads School for Arts & Sciences in Santa Monica, California, marking the culmination of their secondary education journey.

On May 30, Patrick shared a heartfelt moment from the big day on Instagram, posting a photo of himself and his wife, Jillian Dempsey, alongside their 18-year-old sons, both of whom were clad in matching navy-blue graduation robes. The proud father captioned the image: 

“Graduation!! So proud of you boys and cannot wait to see where the next chapter of your lives will take you!”

The post received nearly half a million likes, with Jillian and some of Patrick’s former “Grey’s Anatomy” co-stars congratulating the actor in the comments. Jillian also took to Instagram to post a picture of the twins with their backs to the camera. The celebrity make-up artist, 59, captioned the post:

“C O N G R A T U L A T I O N S 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.”

Apart from Sullivan and Darby, Patrick and Jillian also share a daughter, Talula Dempsey, 23, who was also in attendance at the graduation.

Darby and Sullivan, born on Feb. 1, 2007, have grown up largely out of the public eye, a deliberate choice by their parents to allow them to develop their own identities separate from their father’s fame. Patrick had previously spoken about the challenges of raising children in the spotlight, emphasizing the importance of providing a supportive and nurturing environment. The actor also revealed that his children wanted “to have their own identity, separate from me and that shadow.”

The Dempseys went through a rough patch in 2015, which culminated in Jillian filing for divorce. However, the couple reconciled, and the divorce was called off 22 months after the filing. Now, they are thriving as a family and celebrating their wins together. Patrick and Jillian’s approach to parenting has enabled their children to discover their true selves and develop in line with their unique goals. 

“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 said in an interview, adding they were “all very disciplined on that and you just try to instill the right values.”

In the past, Patrick has emphasized the importance of his children paving their own way and living life on their own terms. He said he also believes in parents supporting their children and allowing them to learn from their mistakes. 

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

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What are your thoughts on this? Do you think more celebrities should raise their children out of the spotlight like the Dempseys? Let us know what you think, and don’t hesitate to forward this to any fans of the Dempseys you might know!