Patrick Dempsey Celebrates Sons’ Graduation with Rare Family Photo

Patrick Dempsey and Jillian Fink celebrated a proud family moment. Their twin sons, Sullivan and Darby, just graduated from high school. The 59-year-old “Grey’s Anatomy” star shared the special moment on Instagram, posting a photo of him and Jillian posing with their boys.

Photo by GABRIEL BOUYS/AFP via Getty Images)

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

The twins, Darby and Sullivan, attended Los Angeles’s private school, Crossroads, which is known for having a high number of celebrity children. Fans and friends, including Patrick’s Grey co-star Justin Chambers, chimed in with congratulatory messages.

Darby also posted a tribute on Instagram, writing, “Couldn’t have asked for a better senior year.” His mom sweetly replied, “My bby B I am so proud of you ❤️❤️,” and his sister Talula, 23, dropped hang-ten emojis.

Patrick and Jillian’s Love Story

Patrick and Jillian’s love story goes back a long way. They met in 1994 when Patrick walked into her Los Angeles salon. Though they were both in relationships at the time, things eventually turned romantic in 1997.

“She was always flirting,” Patrick once told People. Their first date? A homemade dinner at Patrick’s place — and within three months, Jillian had moved in.

They tied the knot in 1999 and in July 2024.

Patrick celebrated their 25th anniversary with a touching tribute on Instagram:

“Life would not be the same without you, your vision, your kindness, your compassion, your love, your sexiness, your intelligence, your warmth, your friendship, your wisdom.”

All About Patrick’s Wife—Jillian Dempsey

Jillian has established a reputation for herself in the beauty industry. She began her career at Delux Beauty, later launching her own cruelty-free and vegan line, Jillian Dempsey Beauty, in 2014.

“With my first brand Delux Beauty, I couldn’t afford to do anything that was natural,” she told Beauty Independent. “I wanted to make my current brand cruelty-free and vegan… and make it really easy to use.”

Photo by John Phillips/Getty Images)

She even turns to her family for honest feedback: “I will always try everything on my family members,” Jillian shared in 2022.

Patrick once said, “My big thing is to make sure the lipsticks taste good when you kiss. And, well, so far they taste pretty darn good.”

In 2020, Jillian launched the FYFE Beauty app, providing users with access to expert tutorials in hair, makeup, and grooming — and, yes, Patrick even made a cameo appearance in a video on covering gray hair during quarantine.

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