Drew Scott, Kenya

The move was bold.

But, to be fair, Property Brothers' Drew Scott and his twin brother Jonathan didn't build their estimated $20 million empire by using an abundance of caution.

So when Linda Phan, the woman who caught his eye at a fashion show, tried to call it a night after sushi and hot chocolate he made a play to keep the evening going. Recalling their first date to People, she said, "I thought, OK, I'm going to duck out and head to this party. And Drew said, 'Oh, I'll come.' And in my head I thought, I didn't really invite you, but sure."

His smooth maneuver paid off. The couple spent the remainder of that 2010 evening singing together at a karaoke party. Or as Phan put it, "Longest first date ever."

And a great setup for the rest of their romance. Though the HGTV personality says he "knew instantly" he wanted to make 32-year-old Phan his bride, he played the long game. Six years after that initial outing—with Phan having already accepted a job as creative director of the siblings' production company, Scott Brothers Entertainment and an invitation to move into their 5,000-square-foot Las Vegas home—he presented her with another offer. "When you have someone as amazing as Linda, it was important to propose," he's said of his elaborately planned overture.

Next month, the real estate agent—marking his milestone 40th birthday today—will follow through on that vow to make Phan his wife. With their unofficial anything goes theme, the weeklong Italian extravaganza is sure to delight. "This is our big day—we can do whatever we want!" Drew explained to People. "One of the things that I love about Linda is that she's with me in that sense. If I want to wear a gold leotard, I'll do it. We're not ones to have a basic white wedding." But their commitment to one another is as traditional as it gets. As he told People, "I want to be with her for the rest of my life."

Drew Scott, Kenya

Drew is the type who believes in love at first sight. For him it's different than lust, it's the feeling "when the person's character just keeps you wanting more," he explained to YourTango in 2013. And it's the sensation he felt when he spotted the Canada native at a 2010 Toronto Fashion Week event. Donning a big cop badge "and giving out tickets for 'bad' fashion," Drew recalled to People, the fun loving artist instantly intrigued. His initial takeaway, he told the mag: "Oh, she's attractive and she has a great personality."

Those compliments didn't roll off the tongue quite so easily when he connected with Phan backstage. Hunting for pizza and sipping on water with one of her three sisters, she was bemused, she told People when "Drew came up to me and said, 'Hey, where'd you get that water?" Groaned Drew, "I was so smooth."

Drew Scott, Kenya

He refined his charms in time for that fateful first date. At the party, he impressed Phan, who has said Disney songs are her go-to in karaoke situations, with his first choice: The Lonely Island's "I'm on a Boat". As Phan recalled, she was smitten the moment "he picked up the microphone."

For Drew the romance was solidified not long after, when he brought Phan to meet his twin brother Jonathan and their high school pal Pedro. As he explained to The New York Times, his trio of boys were so close, they were often finishing each other's jokes. And when Pedro keyed up the setup to a quip, it was Phan who tossed out the punchline, causing Jonathan to whisper in his brother's ear that this woman was a keeper. "In that one moment, I knew we were on the same parallel," he said. "When you're in love, you mesh that way."

Property Brothers, JD Scott, Drew Scott, Jonathan Scott

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Just as his personal life was clicking into place, Drew's career was beginning its meteoric ascent. The aspiring actor and brother Jonathan had been in business together since age 7, when they designed nylon-wrapped, rose-studded hangers. "We would go door-to-door in our neighborhood, and people thought it was cute," Jonathan told Parade. Then one neighbor who owned a chain of American paraphernalia stores in Japan started buying them by the thousands.  

After high school they were eager to break into Hollywood. And as they landed bit parts on Smallville (Drew) and The X-Files (Jonathan) they dreamt up a plan to fund their own projects. Using a $250 down payment, they bought their first $200,000 home and flipped it for a $50,000 profit.

Jonathan Scott, Drew Scott, Guardians of the Galaxy Vol. 2 Premiere

Rich Polk/Getty Images for Disney

"That's where we realized, if we're smart with real estate, we could expand into any passion we had," Drew explained to USA Today. "As we started to grow and flip more properties, I became a real estate agent and started making money as an agent representing clients. Jonathan went to school for real estate design, and we grew our company, Scott Real Estate, where we started to represent clients to renovate their homes and build their homes and commercial projects."

When Drew tried to reignite his acting career in their native Vancouver, he was approached to host real estate shows. "At first, I remember thinking, this is lame—I don't want to be a host, I want to be a superstar, I want to act," he admitted. "The more we talked about it, with our personalities and how we are on our feet, we thought maybe there is something good with hosting; maybe it could give us the opportunity to grow our brand and the businesses that we run, and it did."

Drew Scott, Jonathan Silver Scott, 2015 Creative Arts Emmy Awards

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Their inaugural fixer-upper series Property Brothers made its debut on Canadian cable in 2010, and got picked up by HGTV the following year. And as their empire expanded—their debut series now airs in more than 150 countries and they've produced several spinoffs not to mention a lengthy list of merchandise that includes everything from home décor to original songs—Phan joined the family business.

While she admits some doubted her choice to live and work with her boyfriend, "There's an ease to it," she told People. "You wake up and you go to work. It's nice and really convenient to be able to have meetings with the people you live with."

Drew Scott, Kenya

It helps that her business style meshes well with Drew, who often pushes through long days of filming. "My girlfriend and I are both workaholics," he told YourTango. "We love what we do and that we can work side by side."

Though at first glance, the 6-foot-4 HGTV personality and his 5-foot-2 bride-to-be may appear mismatched, the Canadians are on the same page about everything from a love of food (Drew digs ice cream; Phan favors pizza with goat cheese, olives, spinach, tomatoes, banana peppers and pineapple) to the importance of philanthropy. While Drew says he admires Ellen DeGeneres and Portia De Rossi as a pair because of "all their philanthropic work," Phan has said her dream vacation is "any charitable trip. I'm not one who can sit by the beach and sunbathe all day long. I need to be doing something."

Still, says Drew, he's careful to never stop renovating their union. "It sounds cliché, but communication is the number one way to keep a relationship solid," he says. "You can't just assume that everything is perfect—like anything you are passionate about, ask questions, express your own feelings and take a genuine interest in making the relationship the best it can be."

He took his own advice when putting together his December 2016 proposal. Spending weeks carefully crafting each step, he kept the meticulous details out of his emails and toted the 1.2-carat round-cut solitaire around with him so Phan wouldn't stumble upon either. As he told People, "I've had to be as stealthy as a ninja to pull this off."

Finally, he unfurled his plan during a dinner at Toronto restaurant Piano Piano. He arranged for the Italian eatery to play a version of Train's "Marry Me" that he had recorded himself, the cue for staffers to carry out a custom cake. A play on one of Phan's favorite books, Dr. Seuss' Oh the Places You'll Go, it read "Oh the Places We'll Go," a signal of the adventures that lie ahead. After she accepted, he led her to an engagement party packed with both sets of their parents, his two brothers and a group of friends.

His thoroughness has carried into the making of their destination vows. An impressive run on Dancing With the Stars, a packed shooting schedule and a slew of other friends' weddings they had the maneuver around meant it took the duo nearly a year to lock in a location and a date. "Let me tell you, we're on a plane every two days, whether we're flying somewhere for an appearance on QVC or for our product line or filming," he told E! News last year. But even though they're short on time, they're not glazing over the details.

Often taking advantage of small pockets of time on the set of HGTV's Property Brothers at Home: Drew's Honeymoon House, which saw them renovate their 5-bedroom, 4-bathroom, L.A. dream home, the pair worked down their checklist. Their menu would feature Italian eats, followed by a Magnolia Bakery cake and a late night snack of burgers, fries and Yorkshire pudding. The bridal party would include both of his brothers, Jonathan and J.D. Scott as best man and 14 bridesmaids for Phan. And their first dance would be choreographed with the help of his DWTS partner Emma Slater and her new husband Sasha Farber. As for attire, Drew vowed to wear a kilt in honor of his Scottish heritage while Phan browsed the racks at designer Claire Pettibone's L.A. outpost explaining she was seeking a gown "with a lot of detail" and "maybe a train I won't trip over."

And that's not the only project the DIY- aficionado has taken on. "We're coming up with some handcrafted fun stuff for everybody, designing the cake and designing different aspects of what we want the ceremony to look like," Drew told Us Weekly, noting they're making their wedding bands from scratch. "There are a lot of elements going into it, but the main thing for us is we want to spend time with our family and friends and celebrate."

Drew Scott, J.D. Scott, Jonathan Silver Scott, Emmy Awards 2014

Frazer Harrison/Getty Images

They're looking forward to the weeklong getaway—the extravaganza will air in June on their TLC wedding special, Drew and Linda Say I Do—and the Ecuadorian philanthropy-focused honeymoon that will follow. (In lieu of a registry, they told E! News, they've also asked guests and fans to donate to WE in the hopes of getting 50,000 people in Asia, Africa and Latin America clean water, a nod to line Drew used when they met.)

But Drew already knows what the highlight of the whole affair will be. "Looking into Linda's eyes when she walks down the aisle," he told Us Weekly of the moment he's most looking forward to, "and knowing that's the lady I'm going to be with for the rest of my life."

And when the time comes, he vows he won't even attempt to be smooth: "I'm going to be crying like a fool."

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