The Sweetest Throwback Photos of Brooke Shields and Chris Henchy

Look back on some of the Hollywood couple's most adorable moments over the course of their decades-long relationship

Actress Brooke Shields and director Chris Henchy married in 2001, and more than two decades later, their love is still alive and well. Look back on their love story — which includes the births of daughters Rowan and Grier — through their cute throwback photos together.

Longtime Love

In celebration of their 22-year anniversary, Shields posted an Instagram carousel featuring several sweet photos with her husband.

"22 years married today… sometimes it feels like it’s been forever in the blink of an eye! There’s nobody else I’d rather drive insane or be driven insane by… catch or be caught by… love or be loved by ❤️," Shields wrote, adding, "I’m in it for the long haul. You’re a keeper."

Early Days

The Blue Lagoon star found Henchy in 1999 – or, rather, her bulldog Darla found him. She recounted meeting her husband in her 2005 memoir, Down Came the Rain: My Journey Through Postpartum Depression.

"I had just gotten an American bulldog, Darla, and I brought her to meet friends of mine in the gym on the Warner Bros. lot. While there, the dog wandered off, and Chris brought her back," wrote Shields. "He was writing for a show filmed on the lot and loved dogs. We chatted and he made me laugh."

Forever Date

Since meeting in 1999, the couple has partnered up for a number of events, attending charity fundraisers together and walking red carpets side by side. In April 2000, they dolled up for the GLAAD Media Awards in New York City.

Fun in the Sun

They even make an adorable duo at less formal affairs, like this outdoor fun-run expedition to benefit Breast Cancer Research not long after they met in 1999.

Meant to Be

Henchy proposed to Shields while they were enjoying a romantic getaway in Mexico.

Love Story

Shields and Henchy tied the knot in an intimate ceremony off the California coast on Catalina Island. One month later, they read their vows to each other in Palm Springs. In her loving speech to Henchy, Shields swore to always laugh at his jokes, "even if I've heard them before."

Trusting the Relationship

Shields began seeing Henchy just after splitting from her first husband, Andre Agassi, and she later admitted to having some doubts about finding new love so quickly. In her 2023 PEOPLE interview about her two-part documentary Pretty Baby: Brooke Shields, she remembered worrying that she might be "rebounding," with Henchy, "because I hadn't spent any time sowing my oats," she said.

But after breaking things off with Henchy, she still found herself talking to him frequently.

"I was calling him all the time, and he said, 'You broke up with me, this is the way it works. You don't get to call me every day, because you broke up with me. So don't call me every day,' " Shields recalled, adding that she remembered thinking at the time, "I don't want to lose this person, so I better behave."

Perfect Match

Both husband and wife have a hand in the entertainment biz. Henchy boasts a successful career as a screenwriter and producer, and has worked on hit series like Entourage and Spin City as well as blockbuster comedies like The Other Guys and The Campaign.

Style Savvy

Henchy and Shields complement each other in many ways, including with their fashion tastes. They dressed in matching neutral shades at this 2002 art exhibition and benefit sale.

Goofing Off

These two certainly know how to have a good time! In fact, Shields told PEOPLE that the secret to their lasting romance is laughter.

"He made me laugh and he consistently makes me laugh and doesn't take anything too seriously so I don't go down those rabbit holes the way I used to," she said of Henchy in her 2023 PEOPLE cover story interview. "He sort of just brings me back out and says, 'We'll figure it out.' So he's good at leveling me."

Building a Family

The happy partners became happier parents with the arrival of their first daughter, Rowan Francis, in 2003.

Celebratory Smooch

Baby Rowan joined Mom and Dad in London for Shields' 40th birthday celebration.

Growing Their Home

The adorable trio became a family of four in 2006, when Shields and Henchy welcomed their second daughter, Grier Hammond.

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