Patrick Dempsey Celebrates Twin Sons’ Graduation in Rare Family Photo

Patrick Dempsey Celebrates Twin Sons’ Graduation in Rare Family Photo

Patrick Dempsey and his wife Jillian Fink, both 59, celebrated their twin sons Sullivan and Darby’s graduation from high school.

The boys attended Los Angeles’ private school Crossroads alongside other children of the famous. 

The Grey’s Anatomy alum posted a photo to his Instagram of he and his wife with their boys on graduation day.

‘Graduation!!,’ the proud father’s caption began.

‘So proud of you boys and cannot wait to see where the next chapter of your lives will take you!’

Patrick’s fans and friends left congratulations in the comment section including his former Grey’s Anatomy castmate Justin Chambers, who left a series of clapping hands emojis. 

Patrick Dempsey and his wife Jillian Fink, both 59, celebrated their twin sons, Sullivan and Darby's graduation from high school

Patrick Dempsey and his wife Jillian Fink, both 59, celebrated their twin sons, Sullivan and Darby’s graduation from high school

Darby also posted a selection of photos on Instagram, including one with his sister Talula 23.

‘Couldn’t have asked for a better senior year,’ he captioned the post. 

His mom commented, ‘My bby B I am so proud of you ❤️❤️,’ and his sister posted hang ten emojis in her comment on his post.

Patrick and Jillian have been married since 1999. 

The couple met in 1994 when he was a customer in her Los Angeles hair salon, which she sold in 1998.

Patrick and Jillian were both in relationships when they first met, so things didn’t turn romantic until 1997. 

‘She was always flirting,’ Patrick told People

Patrick made a homemade meal at his home for their first date, and Jillian moved in three months later. 

The Can’t Buy Me Love actor, wrote a sweet tribute to his wife and their marriage for their 25th wedding anniversary in July 2024.

The boys attended Los Angeles ' private school Crossroads alongside other children of the famous

The boys attended Los Angeles ‘ private school Crossroads alongside other children of the famous

Darby with his sister Talula

Darby with his sister Talula  

Patrick and Jillian have been married since 1999. The couple met in 1994 when he was a customer in her Los Angeles hair salon, which she sold in 1998. Seen here with his wife Jillian on May 25, 2025

Patrick and Jillian have been married since 1999. The couple met in 1994 when he was a customer in her Los Angeles hair salon, which she sold in 1998. Seen here with his wife Jillian on May 25, 2025

Patrick's fans and friends left congratulations in the comment section including his former Grey's Anatomy cast made Justin Chambers, who left a series of clapping hands emojis

Patrick’s fans and friends left congratulations in the comment section including his former Grey’s Anatomy cast made Justin Chambers, who left a series of clapping hands emojis

‘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,’ McDreamy wrote on Instagram. 

These days, the mom of three runs her own makeup and skincare line which she got started with the brand Delux Beauty. 

She created a lip gloss just for the cast of Charlie’s Angeles and her products gained cult-like status in the industry, per People.

Jillian started Jillian Dempsey Beauty in 2014.

‘With my first brand Delux Beauty, I couldn’t afford to do anything that was natural,’ Jillian explained to Beauty Independent. 

‘The cost of goods would have been too high. I wanted to make my current brand cruelty-free and vegan, utilizing natural and organic materials where I could find ingredients and making it really easy to use.’ 

Jillian isn’t afraid to turn to her family for help when she needs it. 

‘I will always try everything on my family members, and I absolutely welcome any and all feedback,’ Jillian told the outlet in 2022.

'Graduation!!' the proud father's caption began. 'So proud of you boys and cannot wait to see where the next chapter of your lives will take you!'

‘Graduation!!’ the proud father’s caption began. ‘So proud of you boys and cannot wait to see where the next chapter of your lives will take you!’

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

In 2020, Jillian launched the FYFE Beauty app in which users have access to library of makeup and hair tutorial from experts.

Users can browse videos having to do with hair, makeup, nails, men’s grooming and more.

Patrick appeared in a tutorial from Jillian’s Shelter-in-Place series, where she demonstrated how to cover gray hair.

Previous Article

Nick Hodgson Reunites with Former Kaiser Chiefs Bandmates After Over a Decade

Next Article

Mel B Celebrates 50th with Spice Girls Mel C and Emma Bunton, But Geri and Victoria Are Missing

Write a Comment

Leave a Comment

Subscribe to our Newsletter

Subscribe to our email newsletter to get the latest posts delivered right to your email.
Pure inspiration, zero spam ✨