See Patrick and Jillian Dempsey’s Family Photos as the Couple Celebrates Their 26th Wedding Anniversary

When Jillian Fink saw Patrick Dempsey’s name on the appointment list of her salon back in 1994, she thought it was a joke. As the story goes, Jillian, a renowned hairstylist and makeup artist, owned a salon at the time she met the future McDreamy. One of her employees had a habit of putting celebrities’ names on the appointment list, so when Jillian saw Patrick’s name, she didn’t think much of it. She was pleasantly surprised when he walked into her salon.

“I was shocked,” she previously told PEOPLE. “But at the same time, I was happy because he was so cute.”

The two would form a friendship that didn’t turn romantic until 1997, as they were both in relationships at the time of their meeting. Fast forward two years later, Jillian and Patrick got hitched on July 31, 1999, and the rest is history.

Though their relationship hasn’t been without bumps — the pair briefly split in 2015 — the lovebirds have managed to weather the ups and downs and keep their family together.

“Our marriage was not something I was prepared to let go of,” Patrick told PEOPLE in 2016. “I didn’t feel like we had done all the work. And we both wanted to do that work. That’s where it started.”

Below, see some of Patrick and Jillian Dempsey’s family photos as the couple celebrates their special day.

Where It All Began

For his and Jillian’s 25th anniversary last year, the Grey’s Anatomy star posted this sweet pic from their 1999 nuptials. “25 years, it feels like just yesterday! I can’t get over how quickly the time has gone by,” he wrote in the caption.

Dempsey continued, “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. The love of my life, I’m truly grateful for all that you do and who you are. You’re an incredible mother, wife, friend, and partner .”

Welcome, Talula!

On Feb. 20, 2002, the Dempseys welcomed their first bundle of joy with daughter Talula Fyfe. The daddy-daughter duo are pictured spending some quality time together in this throwback photo.

And Babies Make Five

The Dempseys got double the blessing as they welcomed twin boys Darby and Sullivan five years later on Feb. 1, 2007. From an early age, the Ferrari actor was keenly aware that the boys had starkly different personalities, describing Darby as being “reserved and quiet” compared to Sullivan, whom he said is “very funny — he has funny expressions in the way he’s taking things in.”

Around the World

Dempsey shared this flick of himself and Talula in a ferris wheel for his baby girl’s 23rd birthday earlier this year.

Taking It In

Dempsey was hanging with his boys in this picture he shared on his Instagram.

Bellisima

Patrick and Jillian shared a kiss in this adorable pic taken while the couple was presumably in Italy. “Bellisima,” the actor wrote.

Still the One

“24 years !! What an amazing path we have been on! love you! Happy anniversary,” the Valentine’s Day actor wrote in celebration of their 24th wedding anniversary in 2023.

Celebrating Jillian

And for Mother’s Day 2024, the dotting husband kept it simple writing, “Happy Mother’s Day to the best mom and wife! We love you.”

Gang’s All Here

Years before starring in Ferrari, Dempsey served as producer on 20th Century Fox’s The Art of Racing in the Rain and the entire family was on deck to show support at the film’s premiere in 2019.

Just Us Two

“What a brilliant, compassionate, young woman you have become…so proud of you. You are beautiful inside and out! Love pops!” Dempsey described his daughter as he celebrated her 18th birthday.

Congratulations, Twins

Proud parents Patrick and Jillian pulled up in matching outfits to support their twin boys as they graduated high school.

A Ferrari Type of Night

The Dempsey crew looked ultra-spiffy as they celebrated their patriarch’s blockbuster film, Ferrari in Los Angeles in 2023.

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