11 Sweet Photos of Patrick and Jillian Dempsey in Honor of Their 27th Wedding Anniversary
11 Sweet Photos of Patrick and Jillian Dempsey in Honor of Their 27th Wedding Anniversary
Caroline BlairFri, July 31, 2026 at 10:45 AM UTC
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Patrick Dempsey and Jillian Dempsey during Los Angeles Premiere of “Iron Jawed Angels in 2004; Jillian and Patrick Dempsey at the Charles Finch x CHANEL Pre-BAFTA Party in February 2026Credit: Lee Celano/WireImage; Max Cisotti/Dave Benett/Getty -
Patrick and Jillian Dempsey started dating in 1997 and married two years later on July 31, 1999
The couple are parents to three children: daughter Talula and sons Sullivan and Darby
The actor and the makeup artist celebrated 27 years of marriage on July 31, 2026
Patrick Dempsey and his wife, Jillian Dempsey, have been together for nearly three decades.
The Grey’s Anatomy actor and the professional makeup artist met in 1994 when she was cutting his hair at her salon. Although they enjoyed each other’s company, they were both in relationships at the time, so things didn’t turn romantic until three years later.
“She was always flirting,” Patrick previously told PEOPLE, while recalling that he made her dinner for their first date, and she moved in three months later.
The couple married on July 31, 1999, in Maine and went on to welcome three children together: daughter Talula Fyfe in 2002 and twin sons Sullivan Patrick and Darby Galen in 2007. Although they nearly split in 2015, Dempsey told PEOPLE the following year that their “marriage was not something I was prepared to let go of.”
As Patrick and Jillian Dempsey celebrate 27 years of marriage, take a look back at some of their sweetest photos over the years.
01 of 11
Patrick and Jillian’s July 1999 wedding
After two years of dating, Patrick and Jillian tied the knot on July 31, 1999, during an intimate ceremony on Patrick’s family farm in Maine.
Jillian’s sister, Kristen Mason, told PEOPLE at the time that the Made of Honor actor “saw [Jillian] and started crying” as soon as she began walking down the aisle.
Over the years, the couple have frequently celebrated their wedding anniversary by posting throwback photos from the special day.
“25 years, it feels like just yesterday!” Patrick captioned a wedding photo on Instagram in 2024. “I can’t get over how quickly the time has gone by. 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 @jilliandempsey.”
In 2021, Jillian posted a similar photo and wrote, “JULY 31st 1999 - you do the math! Happy anniversary to my love, Paddy. You make each day brighter. I love you ♥️ wifey.”
02 of 11
The beginning of their red carpet appearances
Jillian Dempsey and Patrick Dempsey at the Emmy Awards in 2001Credit: Gregg DeGuire/WireImage
As Patrick’s acting career started to rise in the early 2000s, his wife was by his side.
Patrick received his first Emmy nomination for his guest actor role in Once and Again and attended the 53rd annual awards show in 2001.
Jillian joined Patrick for the momentous night, and the two posed for photos in matching black outfits.
03 of 11
A family of five
Tallula Dempsey, Patrick Dempsey, Darby Dempsey, Sullivan Dempsey and Jillian Dempsey at the Premiere Of 20th Century Fox’s “The Art Of Racing In The Rain” in 2019.Credit: Albert L. Ortega/Getty
Patrick and Jillian are proud parents to three children and shared their first photos of their daughter Talula and twin sons Sullivan and Darby with PEOPLE in 2007.
“I was a little overwhelmed,” Patrick recalled of finding out they were welcoming twins but added that Talula was “very excited and very good about taking care of her brothers.”
Patrick gifted Jillian a pair of diamond studs after she gave birth to the twins.
“She’s never been more beautiful to me than she is now,” Patrick said of his wife.
The family of five stepped out for the premiere of The Art of Racing in the Rain in August 2019.
04 of 11
Valentine’s Day supporting Valentine’s Day
Jillian and Patrick Dempsey at the ‘Valentine’s Day’ premiere in L.A. in February 2010Credit: Lester Cohen/WireImage
Although Patrick didn’t play the most sincere character in the 2010 movie Valentine’s Day, he made a date night out of the premiere with his wife.
Patrick and Jillian looked lovingly at each other while attending the premiere of the romantic comedy on Feb. 8, 2010.
05 of 11
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Date Night at an Oscars afterparty
Patrick and Jillian Dempsey at the 2017 Vanity Fair Oscar PartyCredit: Dave M. Benett/WireImage
Over the years, Patrick and Jillian have attended many high-profile events — including the Vanity Fair Oscars Party.
The couple looked dapper at the 2017 event, with Jillian in a flowing taupe blouse with a shimmering skirt, and Patrick in a classic black tuxedo.
06 of 11
Returning to where they said ‘I do’
Jillian and Patrick Dempsey in 2018Credit: Patrick Dempsey/Instagram
To celebrate their 19th wedding anniversary in 2018, Patrick and Jillian returned to the gazebo where they got married in Maine. Patrick posted a photo hugging and kissing his wife of nearly two decades outside the memorable place.
“This spot 19 years ago , today !” Patrick captioned the sweet snap.
Meanwhile, Jillian shared a picture of a floral arrangement from her husband and wrote, “Gorgeous arrangement! Happy 19th Anniversary @patrickdempsey 💕💕💕.”
07 of 11
Looking closer than ever
Jillian and Patrick Dempsey in 2022Credit: Patrick Dempsey/Instagram
As the couple have grown in their relationship, they appear to be closer than ever.
For Jillian’s birthday in February 2022, Patrick posted a picture of them hugging.
“Happy Birthday Jill, I love you!” he wrote.
08 of 11
Kisses abroad
Patrick and Jillian Dempsey in February 2022Credit: Patrick Dempsey/Instagram
Patrick and Jillian appeared to be traveling in Italy and shared a sweet kiss in front of a landmark in 2022.
“Bellisima,” the actor captioned the precious picture.
09 of 11
Getting in their steps on their anniversary
Patrick Dempsey and his wife.Credit: Patrick Dempsey/Instagram
To celebrate their 24th anniversary in July 2023, Patrick and Jillian enjoyed a hike together. Patrick beamed in a selfie from the walk, while Jillian smiled and proudly held up her left hand, showing her rings.
“24 years !! What an amazing path we have been on ! love you ! Happy anniversary,” Patrick captioned the picture.
Jillian also shared a snap of Patrick on the hike and wrote, “Happy 24th anniversary Paddy, our hike was incredible.”
10 of 11
All dolled up for Ferrari
Patrick and Jillian Dempsey attend the ‘Ferrari’ premiere in London in December 2023Credit: Joseph Okpako/WireImage
Patrick embraced his real-life love of all things racing by starring in the 2023 biographical sports drama Ferrari.
Jillian showed her support by attending the movie’s premiere on Dec. 4, 2023, in London.
11 of 11
Celebrating their kids
Jillian and Patrick Dempsey with their twin sons in May 2025Credit: Patrick Dempsey/Instagram
Patrick and Jillian’s three children have all marked major milestones over the years. In May 2025, the proud parents posed for photos with their twin boys at their high school graduation.
“Graduation!! So proud of you boys and cannot wait to see where the next chapter of your lives will take you!” Patrick wrote on Instagram.
Meanwhile, Jillian shared a photo of the twins from behind and wrote, “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.”
on People
Source: “AOL Entertainment”
