All of Chip and Joanna Gaines' Most Romantic (and Hilarious) Throwback Pics

Take a walk down memory lane with the adorable 'Fixer Upper' stars on their 20th wedding anniversary 

Chip and Joanna Gaines celebrate their 20th wedding anniversary on May 31, and in honor of our favorite Fixer Upper alumna and all of her laugh-out-loud and swoon-worthy moments with Chip, we've rounded up some of the couple's best throwback photos.

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Newlyweds

Five years ago, when the power couple celebrated 15 years of marriage, Jo reposted this "Just Married" shot to celebrate the milestone.

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Mom and Dad

In 2021, the mom-of-five celebrated her then-16-year-old's birthday with this sweet throwback photo of mom and dad and their first-born!

In the post, she reminisced her little one joining her at work back in the day.

"Drake was my little shop baby and he came to work with me every day," she wrote of her now-18-year-old and recent high school graduate. "I was either wearing him on me or he was sleeping in the pack n play behind the counter. 

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Not Too Crabby

While the pair was all smiles as they feasted over all you can eat crab in this shot from 2014, Joanna admitted "#shouldhavestoppedatroundone."

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Silly Selfie

The couple certainly doesn't take themselves too seriously!

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Vacation Glow

More than a decade ago, the couple posed for this snapshot, which Joanna captioned: "Favorite place with my favorite person," along with the hashtag #roughcreeklodge — a resort in Texas.

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Lights, Camera...

The pair first met in 2001 while Joanna was working at her father's auto shop in Waco, Texas, and Chip was holding down a handful of small businesses. Now, they share five children — Drake, Ella Rose, Duke, Emmie Kay, and Crew.

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Where It Started

Ahead of the final episode of Fixer Upper in 2018, Joanna reflected on the show's early episodes — including this hilarious clip from the pilot.

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Love Abroad

The pair took a trip to Italy together in fall of 2017, and while that's not quite as far of a throwback, their vacation shots were too cute not to include!

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Beauty Sleep

The two caught up on their beauty sleep (for 15 hours!) after arriving in Florence.

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Zoom, Zoom

When in Rome, do as the Romans do ... and hop on a Vespa!

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Keeping the Beat

The two have always marched to the beat of their own drum ...

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Side by Side

… or no drum at all.

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Keeping Cozy

Whether they're shooting hoops in matching adult onesies, catching a concert or taking a romantic getaway together, the stars are constantly making room for quality time: they've got a standing date every Tuesday night.

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Showtime

"We tend to frequent our local holes-in-the-wall for street tacos and queso," Joanna previously told PEOPLE. "After dinner we get ice cream and drive around Waco to go down memory lane and visit our old stomping grounds."

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Fun in the Sun

And sometimes they manage to spice up their date nights by jetting off to a new locale — like their 2017 trip to Mexico.

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Two of a Kind

The duo twinned in green onesies to ring in the New Year in 2017.

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Ready for a Close Up

While the pair makes us seriously swoon with romantic throwbacks, the stars' goofy moments are just as heartwarming. "We take our job seriously… most of the time!" Joanna wrote in her Instagram caption of a promo collage for season 4 of Fixer Upper.

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Fun and Games

They've always been sure to make time for fun — like this moment caught on camera behind the scenes of their show.

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One More Take!

And this one from 2015!

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Funny Faces

Let's not forget this ultra-flattering shot of the pair taking a horse-drawn carriage ride through New York City's Central Park.

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Fourth Time's the Charm

Or these candid selfies! (Remember the good old pre-Instagram carousel days, when you had to fit all your favorite snaps in one shot?)

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Taking the Wheel

She also posted a hysterical #deletedscene of her and her hubby jamming out in the car, screaming along with words they can't quite remember.

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Down to Business

The pair were sweaty but smiling in their matching 'fits when they fixed up this tiny house.

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Behind the Scenes

For your viewing pleasure: another blooper, this time featuring Joanna playfully slapping Chip in the face with a glove.

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Back in the Day

And their long-lasting love story is just one of their successes: the couple has built a home design and lifestyle empire together, which all began back in 2003 when they first opened Magnolia Market.

"I never wore red lipstick but I was feeling bold that day and tried it," Jo wrote in her Instagram caption in 2015. "I was extremely grateful for the forty customers that came in that day to support us. Now 12 years later I'm completely blown away. THANK YOU for all the support, we feel it and are so humbled and grateful!" she continued.

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Fond Memories

The pair have been fixing up houses for years, but Jo credits her design instincts to what she learned from fixing up their first home together. "I remember crying when Chip said we were moving in- it was dumpy and it smelled bad," she admitted in her caption.

"We fixed it up and fell in love with it," she added. "To this day, if you ask us what our favorite house we ever lived in we both go back to this little white 800 sq ft home. We were broke and were forced to be creative with our resources and we were proud as punch about this place. Most of what I learned creatively stemmed from this little fixer upper."

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All Smiles

#TB to when Chip had yet to grace our Instagram feeds with his presence, so Joanna obligingly shared ample content of the happy couple on her own account, especially around their anniversaries.

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Good Old Days

Like this gorgeous then-and-now photo of the pair when they celebrated 12 years of marriage.

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Camera Ready

Or another round of bloopers ...

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Sealed with a Kiss

Back in 2014, Joanna shared this gorgeous throwback of the pair sharing a sweet moment beside a horse stable in honor of their 11th anniversary.

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Wedding Bells

Joanna shared another rare wedding throwback for their 10th anniversary, and the pair continue to look as happy as ever.

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