He couldn't stop looking at her, especially at those soft blue eyes. But how could he approach her? He may have been the most popular driver in the history of NASCAR, a guy whose mere presence made thousands squeal 36 weekends a year at racetracks across America, but there is this little secret about Dale Earnhardt Jr.: He's shy.

He needed a wingman. So on this autumn afternoon in 2008, he convinced T.J. Majors, one of his closest friends who also worked on his race team, to come with him to a meeting where she would be present. Earnhardt was building a new house, and Amy Reimann, an interior designer, was a member of the team that was creating Earnhardt's dream mansion on his 290-acre property outside of Mooresville, North Carolina.

The group sat down at a table. Within minutes, Dale and Amy practically disappeared into each other's eyes. Amy knew nothing of racing—"I wouldn't have been able to pick someone like Jeff Gordon out of a lineup," she said—but they began to date, though Amy had to teach him how.

"Before Amy, I didn't take girls to a dinner or a movie. I'd just say, 'Hey, I'm partying, come over here and let's drink,'" Earnhardt told me a few years ago. "I was spoiled rotten. Everything was about me. Everyone around me did what I said. I didn't listen to anyone. I didn't commit to anything. I was so immature, and I ran myself ragged.

"But then Amy came into my life and changed everything. She taught me what a date was. She got me out of the house, out of my comfort zone. She showed me what it meant to make sacrifices, to honor commitments, to work hard at things."

Before Amy moved into his house in 2011, Dale's worldview didn't extend too far beyond the racetrack: Racing was his oxygen, his everything, his sole reason for climbing out of bed each morning. But then Amy started taking her boyfriend to fine restaurants and introducing him to new foods.

They went to museums together and traveled the globe, experiencing new cultures and new ideas. They eventually grew so close that Dale didn't like to leave the house without her. They were married this past New Year's Eve at a North Carolina winery. Danica Patrick caught the bouquet.

On Wednesday, Earnhardt, who has been voted NASCAR's most popular driver a record 14 straight years, announced he was retiring from the sport at the end of the 2017 season.

I've known Dale since his rookie season of 2000—my first NASCAR story was a diary of Dale's rookie year, and I penned multiple Sports Illustrated cover stories on him—and it's clear to me that she's one of the main reasons he's ready and able to walk away from the sport at the relatively young age of 42.

Make no mistake: Dale Earnhardt Jr.'s retirement is a devastating blow for a sport that, since 2005, has experienced a staggering 45 percent decline in its TV ratings.

Earnhardt—the son of Dale Earnhardt Sr., the seven-time Cup champion who lost his life on a last-lap crash in the 2001 Daytona 500—is the only NASCAR driver today who possesses that incandescent shine of celebrity, the only one with crossover appeal.

He's been on more than 150 magazine covers, ranging from Rolling Stone to GQ to Men's Journal, and he's the only NASCAR driver that, say, a hockey fan in Fargo could recognize and tell you something about.

Where does this leave NASCAR? Many of the top figures who fueled NASCAR's rise in popularity in the early 2000s are now gone; in the last two years, the likes of Jeff Gordon (four titles), Tony Stewart (three titles) and Carl Edwards ($80 million in career winnings) have retired.

With Earnhardt's stepping away at the end of 2017, it seems likely that NASCAR will further recede into the background of the American sporting landscape.

But would it be possible for Dale to make one last charge at his first championship this summer and fall? Could he summon the Earnhardt magic one more time, in the twilight? If he does, it could end up being the most compelling NASCAR story in a long, long time.

We were rolling down Highway 136 outside of Mooresville, North Carolina, in Dale's 1971 cherry-red Corvette convertible, his favorite toy, and cruising through the blue-sky afternoon. It was August 2000, and as Dale mashed the accelerator he shared a confession. "The key to all the success I've had is my daddy," he said. "It's that simple. He's taught me how to drive, how to live with integrity and how to be a man."

I went back to North Carolina a few weeks later for a profile on Dale Sr. Upon seeing me, the man known as the Intimidator growled, "What, they sent the f--king intern!" I froze for one heartbeat, two, three…then Big E laughed and waved me over. He later told me, "You better treat my boy right."

Only a few months after uttering those words, Dale Sr. hit the wall at Daytona at 200 mph in February 2001, his head nearly being ripped off in a crash a mile from the finish line of the Great American Race. Over the next dozen years, Dale and I would have multiple conversations about his daddy—as he still refers to him—and the day everything in Dale's world changed.

I've often thought that this dark moment in his life explains part of his mass appeal; sports fans across the world witnessed his father's death, and in that instant they connected and empathized with Dale in a way we don't with other athletes. And as millions watched the son grieve, even casual fans became emotionally invested in him, hoping for Dale's sake that he could find some sort of redemption on the racetrack.

"It's hard to always be measured against my daddy, but I wouldn't want it any other way," Dale told me a few months after his father died. "My goal was to always make my daddy proud. Now that's what I'm going to try to do moving forward."

It wasn't easy. In those ensuing years, he partied a lot—he kept 13 cases of beer in a cooler in his basement, which he dubbed "Club E"—and he sometimes missed early-morning interviews or other commitments.

But his fans identified with him. You see, he was one of them, a blue jean-wearing, hell-raising good ol' boy whose fans lived vicariously through him as Dale won three races in 2001 after his dad died. In NASCAR circles, it was taken as an article of faith that Dale would someday win a championship.

I spent more time with Dale before the 2004 Daytona 500. That week, he repeatedly looked at a picture that he kept in his motorhome. In the old yellowed photograph he was six years old, and his string-bean arms were wrapped around the neck of his daddy. The photograph, shot near the Earnhardt farm in Mooresville in 1980, captured the father tenderly patting his towheaded youngest son on the back.

Dale didn't often say it, but he missed his dad terribly, especially when he was at Daytona. After he won the 500 that Sunday night, he jumped out of his car and, with wet eyes, blew a kiss to the sky. It remains one of the most authentic, emotional moments I've ever witnessed at a sporting event.

Late that night, after I had spent time talking to Dale, I remember thinking, I sure hope he has someone special to share this with.

For several years, sportswriters across the country were brutal on Dale, many calling him the most overrated athlete in America. From 2009 to 2012, he endured a 143-race winless streak. In what should have been the prime years of his career, he floundered in the middle of the pack.

In truth, Dale really isn't anything like his daddy, who was a man's man who hunted at dawn, worked his farm by day and drove racecars like he was mad as hell. Dale is introverted, loves to play racing games on his computer and is a people pleaser. I never met another driver (or reporter) who didn't like him.

But I also worried about him then, because his greatest fear in life is letting others down. At one point during his winless streak, I asked Dale, You got anyone to talk to?

"Well," he said one afternoon at the track in Phoenix, "I have met a girl."

He then flashed the wickedest smile I'd ever seen.

It was approaching 2:30 a.m. on Feb. 24, 2014. Hours earlier, Dale had just won his second Daytona 500, and now he was walking through the track's infield. Dale and Amy, hand in hand, stepped through the cool Florida darkness.

They climbed into Dale's new motorhome. Amy took a seat. Dale grabbed a Coors Light bottle from the refrigerator and then picked up his smart phone. He had long resisted joining Twitter, wanting to protect his privacy. But now he pounded out his first tweet: "Tonight seemed like as good as any to join Twitter. How is everyone doing?" Within minutes, he had more than 230,000 followers, a number that has now grown to 2.09 million.  

Dale's hardcore party days were a thing of the past; now he didn't drink alcohol four days before a race, more evidence of the discipline Amy had infused in his life. Now the party consisted of the three of us. Dale sipped his beer and looked out into the empty Daytona infield, sitting so close to the spot where his daddy lost his life.

"I think of daddy when I'm here, but not the way people might imagine," he said, "It's OK that he lost his life here. He died driving a racecar, his love. I'm OK with that. I feel good here now. I have good feelings about him. I think he'd be proud now."

"I've seen a change in Dale," Amy said back then. "He's not as concerned with what people think of him. He's more joyful about life in general."

Here with Dale and Amy, I didn't realize it at the time, but this was the beginning of the end of his NASCAR career. Now I can see that this was as good as it possibly could have gotten for Dale Earnhardt Jr.—winning the biggest race of the year, NASCAR's Super Bowl, for the second time (his dad only won it once) and doing it with the woman he loved by his side for the first time.

At this very moment, at this hallowed place for Dale, his dreams had materialized—in racing and in life.

Dale knows the danger of racing as well as anyone on this planet. In 2012, he thought he was a goner when he blew a tire and slammed into the wall at nearly 190 mph at Kansas Speedway during a test session. Weeks later, he got pummeled during a harrowing 25-car crash at Talladega Superspeedway. In each instance, he suffered a concussion. He sat out the last two races of that season.

Then last June he took another hard hit at Michigan International Speedway and again was concussed. He missed the last 18 races of 2016.

Amy was with him for each step of his extensive rehab. "It was just me and Amy," Earnhardt said in a press conference Wednesday. "Without her help in those days of recovery, I wouldn't have been able to return to the track this season."

Dale has 26 career wins, a feat that only 30 others have accomplished in the 69-year history of NASCAR. But he's struggled this season. Through eight races, his average finish is 23.8, which is on pace to be the lowest of his career.

Drivers tend to lose their willingness to take chances in NASCAR in their early 40s. Races are won by drivers who can motor through the corners the fastest, by drivers who can live on that precarious edge of nearly being out of control. After so many hits—and in Dale's case, so many concussions—it's only natural for a driver to grow more conservative.

Still, it only takes one win in the first 26 races to qualify for the playoffs. And if he makes it into the postseason, well, you never know.