Chip and Joanna Gaines' love story and lifestyle empire are equal parts inspirational and aspirational — but they almost didn't happen at all. A lackluster first date and a $50 bet nearly prevented the future house-flipping gurus from getting together, but eventually, they reconnected and went on to become the down-to-earth HGTV stars fans know today.

"Match made in heaven is not the term you would use to describe us," Joanna previously told PEOPLE. "But when we mixed our personalities together, it created a spark."

That spark has led to their fame and family (the couple share five kids: ​​Drake, Ella Rose, Duke, Emmie Kay and Crew) as well as their Magnolia empire, which now comprises of a quarterly journal, a TV network, multiple retail stores, a real estate company, rental properties, a restaurant and more.

The couple, who married in 2003, often share sweet tributes to one another on social media, while also staying candid about the work it takes to balance their relationship, businesses and family life.

​​"Jo and I both made a commitment pretty early on that the two of us are the most important variable," Chip previously told PEOPLE. "If we can figure out how to be right as a couple, then obviously we have a lot better opportunity to be right for our kids."

From their first date to a hit HGTV show, here's a complete timeline of Chip and Joanna Gaines' relationship.

The future HGTV stars met in the waiting room of Joanna's dad's auto shop in Waco, Texas, back in 2001. While Joanna had actually been eyeing Chip's roommate, "Hot John," it was Chip who asked her out, and she agreed to go on a date with him.

Chip almost lost his chance when he picked her up an hour and a half late, she recounted. "He didn't apologize for being late, either. He had so much confidence. I don't know. I can't explain it. Only Chip could be an hour and a half late and have no one mad about it," Joanna wrote.

As they started talking, Joanna wasn't entirely convinced they were a match. "It wasn't love at first sight for Chip and me. For one thing, I was typically attracted to guys who were more on the quiet side," Joanna wrote in an essay for Magnolia Journal. As Chip talked about all the companies he dreamed of launching and risks he was eager to take (hello, house flipping!), Joanna found herself "wondering if he was just a bit crazy," adding that she initially figured they wouldn't go out again.

Despite her initial hesitations, the pair ultimately did go on that second date — but not until a few months later, when Chip finally called to ask her out again. "I'd made a bet with Hot John to see who could hold out the longest before calling our dates back," Chip explained in the couple's joint memoir, The Magnolia Story. "I really wanted that fifty dollars from John! That's the only reason I didn't call."

Joanna realized that she enjoyed the way he saw the world "through the lens of untapped potential," she later wrote, adding that it helped her better see her own potential. ​​"This near-stranger had drawn out a side of me that I didn't yet know existed," she continued. "My gut told me there was something there worth waiting for. Our lives have beat to this same rhythm ever since."

Once the pair reconnected, the rest was history. They dated for a year before Chip popped the question, initially pretending that he was taking Joanna to a concert a few hours outside of Waco. Instead, he drove her to a shopping center near the town where his parents grew up, and proposed before taking her to design her own engagement ring at a jewelry store run by his dad's friend, Billy Holder.

"I was able to pick out a nice round diamond and a beautiful, antique-looking platinum setting. I had a blast sitting there with Billy, designing the perfect ring. Chip just sat there, patiently observing every second of it," Joanna wrote.

The surprises didn't end there: the newly engaged pair went to dinner at a hotel, where their families were waiting to congratulate them. "My parents, my little sister, Chip's parents, and his sister were all there waiting to celebrate our engagement with us," Joanna added.

The following year, the pair said "I do" at ​​the historic Earle-Harrison House in Waco, Texas. For the big day, Joanna wore a strapless white gown and a delicate tiara. Following the nuptials, the bride and groom posed for photos in a vintage car with a "Just Married" sign on the back.

After their honeymoon, the couple got right to work, with Joanna joining in on Chip's house-flipping venture. One of their first projects was their own home — a "dumpy" place that "smelled bad," Joanna recalled.

"To this day, if you ask us what our favorite house we ever lived in we both go back to this little white 800-square-foot home," she added, sharing a photo of the house on Instagram. "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."

It took some time for the two to figure out how best to collaborate. ​​"Early on we had our fair share of fights and figuring out where the boundaries were," said Joanna. "He's good at the big picture, and he's good at risk. I like the details."

A few months after tying the knot, the pair launched their first venture together: Magnolia Market in Waco. In order to open the space, they borrowed $5,000 and opened what would become their flagship retail store. "I was extremely grateful for the forty customers that came in that day to support us," Joanna wrote on Instagram.

In 2005, the couple welcomed their first child, son Drake, who has made several cameos on Fixer Upper over the years.

In 2006, the pair welcomed baby number two: their first daughter, Ella Rose. From there, they continued to add to their brood, welcoming son Duke in 2008, and daughter Emmie Kay in 2010. Fans of Chip and Joanna have watched their little ones grow up on the show and in glimpses on social media over the years.

"Family is the most important thing in the world," Joanna later told PEOPLE. For Chip and Joanna, part of prioritizing their family has meant making sure their children have a life away from the spotlight. "They're so young, and we want to give them the chance to have a normal childhood," she said.

In 2011, Joanna was approached by Katie Neff, an executive at High Noon production company, after Neff came across a blog about Joanna's family and house-flipping work. At the time, Chip and Joanna's business was just the two of them and occasionally a few subcontractors for larger projects, according to Texas Monthly.

After filming a sizzle reel, Neff began pitching the show to networks — and it was quickly scooped up by HGTV.

The Gaineses shot to stardom overnight when Fixer Upper aired on HGTV. The show was renewed for five seasons with an option for a sixth.

"I think it is their perfect imperfections," Allison Page, HGTV and DIY Network's general manager, said of the show's instant success to Texas Monthly. "They have the kind of marriage and family you'd want. It's not perfect. He does silly things, and they occasionally trip over their words or sweat on each other. They are the best of what's real in life. It's not a kind of fantasy — perfected, glossy, everything works every second. There's an authenticity in their relationship and that comes through in the show."

Following the uber-successful launch of Fixer Upper, the freshly famous duo bought a pair of abandoned cotton silos in downtown Waco, where they moved Magnolia Market and hoped to generate some business in the town that they loved.

"We believe in the growth of our city, and we think the most potential is in the heart of it, which is downtown," Joanna told Texas Monthly.

Over the course of 2016 and 2017, Chip and Joanna ramped up their entrepreneurial enterprises in almost every capacity imaginable: They launched The Magnolia Journal; opened a bed and breakfast and a café; published their memoir; created paint, rug, wallpaper and furniture lines; and continued to film Fixer Upper while raising four kids.

After five seasons of the dynamic duo revitalizing Waco one home at a time, they announced that Fixer Upper would be coming to an end.

"It is with both sadness and expectation that we share the news that season 5 of Fixer Upper will be our last," they announced on their blog. "While we are confident that this is the right choice for us, it has for sure not been an easy one to come to terms with. Our family has grown up alongside yours, and we have felt you rooting us on from the other side of the screen. How bittersweet to say goodbye to the very thing that introduced us all in the first place."

As the pair continued to expand their home improvement empire, they launched their Target collaboration, Hearth & Hand with Magnolia, ahead of the 2017 holiday season.

After previously hinting that they hoped to expand their family — with Joanna even saying that she wanted twins — the couple revealed that they were expecting again in 2018.

"Gaines party of 7.. (If you're still confused.. WE ARE PREGNANT)," the proud dad captioned a playful photo of the pair showing off "matching" baby bumps.

And baby makes seven! Two days after baby Crew's arrival, the new dad announced his son's birth on Twitter.

"And then there were 5.. The Gaines crew is now 1 stronger! 10 beautiful toes and 10 beautiful fingers all accounted for, and big momma is doing great! #blessedBeyondBelief," Chip wrote.

Continuing his tradition of surprising his family with new pets, Chip brought home a puppy at the end of summer 2019.

"Chip told me he hadn't surprised us in a while with a new animal and that it was long overdue... we now have more dogs than children 😂 #englishmastiff," Joanna announced on Instagram.

The pup joined the Gaines crew's ever-expanding menagerie, which then included six dogs as well as a number of cats, cows, horses, chickens and goats.

Fixer Upper fans rejoiced at the news that the Gaineses would be returning to the small screen with Fixer Upper: Welcome Home two years after the original show ended. The reboot was slated to air on the couple's Magnolia Network — a rebrand of DIY Network, in partnership with Discovery Channel. The network was initially slated to launch in October 2020 but was pushed back several times due to the pandemic.

"The day we wrapped our final episode of ​Fixer Upper,​ we really believed it was a chapter closed," Chip and Joanna said of the series. "We knew we needed a break and a moment to catch our breath. But we also knew we weren't done dreaming about ways to make old things new again."

Welcome Home eventually premiered on Discovery+ on Jan. 29, 2021.

Chip and Joanna aren't shy about posting sweet tributes to each other on social media, whether it's to celebrate an anniversary or an everyday moment. To mark 18 years since saying "I do," Joanna posted a slideshow of photos and videos with her husband and their kids on a tropical getaway.

"18 years. Thankful to be on this adventure with you—happy anniversary @chipgaines ❤️," she captioned the post.

The couple kicked off 2022 with the long-awaited launch of Magnolia Network, their joint venture with Discovery+. The network is the cable home to Fixer Upper: Welcome Home, as well as an enormous and ever-expanding slate of original food, home and lifestyle content, including Magnolia Table, Restoration Road with Clint Harp, Family Dinner, The Johnnyswim Show, Mind for Design and Zoë Bakes.

Speaking about their hopes for the network in a December 2021 press release, the couple said, "It wasn't long ago that watching TV meant time together as a family. It was a place where people of all ages could gather and be informed, entertained, and inspired by the kind of honest, authentic programming that brings people closer." They continued, "That's what we've set out to build with Magnolia Network, and we've been amazed by the stories and storytellers we've found, people whose lives are living proof that our world is full of beauty, hope, courage, and curiosity."

"I think comfortable for us can be a little dangerous," Joanna once told PEOPLE. "The second Chip gets content, he gets really restless. It's not about, 'Let's get here and then we'll be happy.' We like the idea of having to wrestle a little bit and figure things out. That's where we thrive the most."

In May, Chip and Joanna announced their plans to renovate a nineteenth-century castle in their hometown — which they had been trying to purchase for 20 years.

"For nearly two decades, Chip watched and waited, persistently putting in offers whenever the castle was relisted — each one passed over for someone else, while very few improvements appeared to be made," Joanna wrote in 2019.

They also revealed that the project would air in a special eight-episode series titled Fixer Upper: Welcome Home - The Castle in September.

Joanna wrote a personal essay for the fall 2022 issue of Magnolia Journal and spoke about her relationship with Chip and the obstacles they've had to overcome together.

"In our 20 years of marriage, Chip and I have experienced a little bit of all of it," Joanna said. "Losing a loved one. Shifts in friendships. Bills we couldn't pay. Moments where our hearts were broken. Times when all hope felt lost and circumstances were out of our control. When all I could think to do was lay face down on the floor in surrender."

Joanna reminisced on her 2003 wedding during an interview with PEOPLE. "My favorite moment is when we said goodbye to everybody, got in the limo and ate so much food!" she said.

"I just remember, when we got there, I saw how good the food looked and I asked my mom, 'No matter what, will you just put some food in a container and put it in the car?' " the designer recalled.

"So we did our thing, we did our dance, we did all the things that you're supposed to do at a wedding. And all I kept saying is, I can't wait to be in that car with Chip headed to our honeymoon. And the second that door shut, I was like, 'Thank God, this is why I'm here. I just wanna be with you and I wanna eat.' "

Joanna went on to say it's easy to lose sight of what's most important during a busy event. "Weddings are kind of scripted and you're doing a lot," she said. "You can forget why you're really there. And for me, I was really there because I wanted to be with Chip. It will always be my favorite memory — when that limo door shut and we just ate like kids with our hands. It was Beef Wellington, mashed potatoes and two different kinds of cake."

By clicking “Accept All Cookies”, you agree to the storing of cookies on your device to enhance site navigation, analyze site usage, and assist in our marketing efforts.