Ask any NASCAR driver, and they’ll tell you: there’s nothing quite like the passion and unpredictability of NASCAR fans. These are folks who camp out for days at the track, fly their favorite driver’s colors, and transform race weekends into miniature festivals of speed, barbecue, and camaraderie. Some fans have even turned their homes into mini NASCAR museums.

It’s completely decked out in vintage diecast cars, autographs, and decades’ worth of memorabilia, all dedicated to their singular racing heroes. But every once in a while, the passion crosses into territory you just can’t plan for. And, most importantly, can’t forget. Just ask Dale Jr., who still remembers a fan encounter from the late ’90s that was so bizarre, it’s stuck with him for decades.

Dale Jr.’s awkward fan moment

Dale Earnhardt Jr. has spent his whole life surrounded by NASCAR royalty, a natural consequence of being the son of the legendary Dale Earnhardt Sr. From his earliest days, racing wasn’t just a sport. Rather, it was the backdrop of his everyday life. “Dad’s buddies, you know, they would kind of put you in these scenarios that were awkward like that,” Dale Jr. recalled, hinting that life in the fast lane sometimes meant more than just cars and trophies.

On the latest Bless Your ‘Hardt podcast, Junior shared one such unforgettable moment that could only happen when you carry the Earnhardt name. “There was a lady that was excited about, um, meeting me, or meeting an Earnhardt of any kind,” he said. And that’s no exaggeration; the Earnhardt fan base has always been fiercely loyal and incredibly passionate. For many, meeting any member of the family is a once-in-a-lifetime event.

But this meeting wasn’t exactly a polite handshake and a selfie like in most cases. Dale Jr. painted the scene: “It was, you know, six, seven o’clock in the evening… there’s a lady standing there. She’s older than me but not, not a ton, and they’re like, ‘She wanted to meet you so bad. She’s a big fan of yours.’ And she just pulled her shirt down.”

Caught off guard but going along with the moment, Junior did what any good sport in his position might do. He signed on her cleavage. Amy Earnhardt was more concerned about the venue. “Not like signing your cleavage like at the racetrack tastefully in front of other people?” she said, pulling Dale Jr.’s leg.

And for Dale, “It was awkward.” He admitted with a laugh, recalling how surreal it felt in the moment. For Dale Jr., the incident was just another strange perk of growing up as racing royalty. It was a reminder that in NASCAR culture, the Earnhardt name inspires a level of devotion that can sometimes cross into hilariously awkward territory.

Not the only time Dale Jr. was caught in an awkward spot

If you thought Dale Jr.’s recent story about being unexpectedly pulled into the spotlight was peak awkward, well, it wasn’t his first rodeo. In fact, Dale Jr. has had his fair share of moments that made him want to just melt into the floor. And one particular birthday still holds the crown.

“I think for my 18th or 21st birthday, one of them two, they had a ‘lady cop’ show up to the Deerhead shop,” Dale Jr. recalled. “I was racing probably late models around this time.” According to him, it was all part of another one of Dale Earnhardt Sr.’s friends’ well-planned pranks.

“They put me in a chair right in the middle of the floor in front of everybody,” he said. “And she stripped. It was a setup, and it was really embarrassing. And all the guys, they’re laughing.” It’s clear Dale Jr. wasn’t exactly in on the joke. He even admits the whole scene is immortalized (unfortunately) through photographic evidence.

“I have pictures of this event,” he said. “Not like me and her like, ‘Hey, let’s grab a photo.’ I have a couple of pictures of it happening, and they’re terrible.” Before anyone jumps to conclusions, he made it clear the “lady cop” didn’t actually take things too far. “I mean, she didn’t get naked,” he explained. “She just kind of had a little dance.”

It’s the kind of story that perfectly sums up Dale Sr.’s friends. They were always looking for the next opportunity to put him on the spot. Cameras ready and with a sense of humor that toes the line between hilarious and humiliating.

Whether it’s a public setup or a birthday surprise gone rogue, Dale Jr. has proven time and again that he can laugh it off. Even if he’s still cringing years later.